WO2021259208A1 - Tyk-2 inhibitor - Google Patents
Tyk-2 inhibitor Download PDFInfo
- Publication number
- WO2021259208A1 WO2021259208A1 PCT/CN2021/101282 CN2021101282W WO2021259208A1 WO 2021259208 A1 WO2021259208 A1 WO 2021259208A1 CN 2021101282 W CN2021101282 W CN 2021101282W WO 2021259208 A1 WO2021259208 A1 WO 2021259208A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pyridin
- amino
- acetamide
- methylsulfonyl
- alkyl
- Prior art date
Links
- 229940123371 Tyrosine kinase 2 inhibitor Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 4
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 4
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 3
- -1 methoxy, ethoxy Chemical group 0.000 claims description 563
- 229910052736 halogen Inorganic materials 0.000 claims description 302
- 150000002367 halogens Chemical class 0.000 claims description 271
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 233
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 230
- 125000000623 heterocyclic group Chemical group 0.000 claims description 199
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 142
- 238000006467 substitution reaction Methods 0.000 claims description 91
- 125000001424 substituent group Chemical group 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 88
- 239000001257 hydrogen Substances 0.000 claims description 88
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 229910052757 nitrogen Inorganic materials 0.000 claims description 75
- 125000001072 heteroaryl group Chemical group 0.000 claims description 70
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 64
- 125000005842 heteroatom Chemical group 0.000 claims description 61
- 150000002431 hydrogen Chemical class 0.000 claims description 55
- 229910052760 oxygen Inorganic materials 0.000 claims description 52
- 239000001301 oxygen Substances 0.000 claims description 52
- 229910052717 sulfur Inorganic materials 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 48
- 239000011593 sulfur Substances 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 40
- 125000004122 cyclic group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000002619 bicyclic group Chemical group 0.000 claims description 27
- 125000004043 oxo group Chemical group O=* 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 24
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 23
- 229910052805 deuterium Inorganic materials 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 20
- 125000002757 morpholinyl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 16
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 16
- 125000002393 azetidinyl group Chemical group 0.000 claims description 15
- 125000003386 piperidinyl group Chemical group 0.000 claims description 15
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 9
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 8
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 8
- 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 8
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 8
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 8
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 6
- XKVITUMJUHNQHP-CALCHBBNSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1 XKVITUMJUHNQHP-CALCHBBNSA-N 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- AYWHUNIHMQUGRP-UHFFFAOYSA-N CC(NC(C=C1NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1C1=CC=CN=N1)=O Chemical compound CC(NC(C=C1NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1C1=CC=CN=N1)=O AYWHUNIHMQUGRP-UHFFFAOYSA-N 0.000 claims description 4
- LKRZSJNSORSCQK-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C1=NC=CC=C1)=O LKRZSJNSORSCQK-UHFFFAOYSA-N 0.000 claims description 4
- QWGHRQRBZOWQHS-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1OCCOC)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1OCCOC)=O QWGHRQRBZOWQHS-UHFFFAOYSA-N 0.000 claims description 4
- AYFFFMQSJZFSTO-UHFFFAOYSA-N CC(NC1=NC=C(C2=CNC=N2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CNC=N2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O AYFFFMQSJZFSTO-UHFFFAOYSA-N 0.000 claims description 4
- CWOYECWEESTZSV-UHFFFAOYSA-N CC(NC1=NC=C(C2OCCC2)C(NC2=CC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2OCCC2)C(NC2=CC(S(C)(=O)=O)=CC=C2)=C1)=O CWOYECWEESTZSV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000005902 4,5,6,7-tetrahydrofuro[3,2-c]pyridinyl group Chemical group 0.000 claims description 3
- KVAMXMXEDNSDGA-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C1=NC=C(COC)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C1=NC=C(COC)C=C1)=O KVAMXMXEDNSDGA-UHFFFAOYSA-N 0.000 claims description 3
- XYIMCSWGGGPZNO-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O XYIMCSWGGGPZNO-UHFFFAOYSA-N 0.000 claims description 3
- KEIGGTSBOIAQRO-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1C(C=C1)=NC=C1F)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1C(C=C1)=NC=C1F)=O KEIGGTSBOIAQRO-UHFFFAOYSA-N 0.000 claims description 3
- FPPFOVFVSMJGMQ-IYBDPMFKSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OC)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OC)=C1 FPPFOVFVSMJGMQ-IYBDPMFKSA-N 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 3
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 3
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 3
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 3
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- GTMUHOMZGRNVHL-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C(N=N2)=CC=C2OC)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C(N=N2)=CC=C2OC)=NC(S(C)(=O)=O)=C1 GTMUHOMZGRNVHL-UHFFFAOYSA-N 0.000 claims description 2
- XGMQFJBAWFPMPH-JWTNVVGKSA-N CC(C1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1)OC Chemical compound CC(C1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1)OC XGMQFJBAWFPMPH-JWTNVVGKSA-N 0.000 claims description 2
- UHXRUYXZOHFCRQ-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OCC3CC3)=C2)=NC=C1C(N=N1)=CC=C1OC)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OCC3CC3)=C2)=NC=C1C(N=N1)=CC=C1OC)=O UHXRUYXZOHFCRQ-UHFFFAOYSA-N 0.000 claims description 2
- XZJRZKSJJAFNBZ-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1N(CCOC1)C1=O)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1N(CCOC1)C1=O)=O XZJRZKSJJAFNBZ-UHFFFAOYSA-N 0.000 claims description 2
- AUNJWUHTISZPAC-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C(C=C1)=NC=C1F)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C(C=C1)=NC=C1F)=O AUNJWUHTISZPAC-UHFFFAOYSA-N 0.000 claims description 2
- ZLTPFMGVVIEXNQ-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C3CC3)=C2)=C1C(C=C1)=NC=C1F)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C3CC3)=C2)=C1C(C=C1)=NC=C1F)=O ZLTPFMGVVIEXNQ-UHFFFAOYSA-N 0.000 claims description 2
- RISHPLABLRKNLN-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OC)=C2OC)=C1C(C=C1)=NC=C1F)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OC)=C2OC)=C1C(C=C1)=NC=C1F)=O RISHPLABLRKNLN-UHFFFAOYSA-N 0.000 claims description 2
- DPDPCMUXPHWECM-KDURUIRLSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2CCOCC2)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2CCOCC2)=C1 DPDPCMUXPHWECM-KDURUIRLSA-N 0.000 claims description 2
- HJSSLXFPBZUVFN-GASCZTMLSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CN=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CN=C1 HJSSLXFPBZUVFN-GASCZTMLSA-N 0.000 claims description 2
- KEIGGTSBOIAQRO-BMSJAHLVSA-N [2H]C([2H])([2H])OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2F)=NC(S(C)(=O)=O)=C1 Chemical compound [2H]C([2H])([2H])OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2F)=NC(S(C)(=O)=O)=C1 KEIGGTSBOIAQRO-BMSJAHLVSA-N 0.000 claims description 2
- FPPFOVFVSMJGMQ-DNPDIFGOSA-N [2H]C([2H])([2H])OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1 Chemical compound [2H]C([2H])([2H])OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1 FPPFOVFVSMJGMQ-DNPDIFGOSA-N 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- OKMPBEGEWKZYOG-UHFFFAOYSA-N CC(C)(C1=CN=C(C(C=NC(NC(C)=O)=C2)=C2NC2=NC(S(C)(=O)=O)=CC(C)=C2)C(F)=C1)O Chemical compound CC(C)(C1=CN=C(C(C=NC(NC(C)=O)=C2)=C2NC2=NC(S(C)(=O)=O)=CC(C)=C2)C(F)=C1)O OKMPBEGEWKZYOG-UHFFFAOYSA-N 0.000 claims 2
- ANXYMZZLRSQWQW-UHFFFAOYSA-N CC(C)OC1=CC(S(C)(=O)=O)=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=C1 Chemical compound CC(C)OC1=CC(S(C)(=O)=O)=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=C1 ANXYMZZLRSQWQW-UHFFFAOYSA-N 0.000 claims 2
- YFOIXFGCEOOROT-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=NC=C1C(N=C1)=CC2=C1OCCO2)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=NC=C1C(N=C1)=CC2=C1OCCO2)=O YFOIXFGCEOOROT-UHFFFAOYSA-N 0.000 claims 2
- DKWVHXLTFDFCHO-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC3=C2CCCO3)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC3=C2CCCO3)=C1)=O DKWVHXLTFDFCHO-UHFFFAOYSA-N 0.000 claims 2
- NWJIYIFULWLVRD-UHFFFAOYSA-N CC(C(C=CN=C1)=C1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(C(C=CN=C1)=C1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)O NWJIYIFULWLVRD-UHFFFAOYSA-N 0.000 claims 1
- AEBVAUPNQPAVNZ-UHFFFAOYSA-N CC(C(C=CN=C1)=C1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)OC Chemical compound CC(C(C=CN=C1)=C1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)OC AEBVAUPNQPAVNZ-UHFFFAOYSA-N 0.000 claims 1
- BBQFDGQKWQVWCI-UHFFFAOYSA-N CC(C)(C(C(C)=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1)O Chemical compound CC(C)(C(C(C)=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1)O BBQFDGQKWQVWCI-UHFFFAOYSA-N 0.000 claims 1
- FYTULFPXUJHEKD-UHFFFAOYSA-N CC(C)(C(C(Cl)=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC=C1)O Chemical compound CC(C)(C(C(Cl)=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC=C1)O FYTULFPXUJHEKD-UHFFFAOYSA-N 0.000 claims 1
- KVQSFMSZBOJPBT-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC(C=C1)=NC(S(C)(=O)=O)=C1F)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC(C=C1)=NC(S(C)(=O)=O)=C1F)O KVQSFMSZBOJPBT-UHFFFAOYSA-N 0.000 claims 1
- UEZKQLREGKCENJ-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=C(C)C=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=C(C)C=CC(S(C)(=O)=O)=C1)O UEZKQLREGKCENJ-UHFFFAOYSA-N 0.000 claims 1
- RILXOTUPSMPNQO-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(C#N)=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(C#N)=CC(S(C)(=O)=O)=C1)O RILXOTUPSMPNQO-UHFFFAOYSA-N 0.000 claims 1
- ZEUXCBCUBWOVNW-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(C(F)F)=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(C(F)F)=CC(S(C)(=O)=O)=C1)O ZEUXCBCUBWOVNW-UHFFFAOYSA-N 0.000 claims 1
- RCQXDPIRPHFKAP-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(C)=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(C)=CC(S(C)(=O)=O)=C1)O RCQXDPIRPHFKAP-UHFFFAOYSA-N 0.000 claims 1
- AQSBFTYMWHDZLA-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(COC)=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(COC)=CC(S(C)(=O)=O)=C1)O AQSBFTYMWHDZLA-UHFFFAOYSA-N 0.000 claims 1
- BQKNPGBABPVYTO-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(F)=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(F)=CC(S(C)(=O)=O)=C1)O BQKNPGBABPVYTO-UHFFFAOYSA-N 0.000 claims 1
- UQCIMMPORGZRJA-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(N(CC2)CC2O)=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(N(CC2)CC2O)=CC(S(C)(=O)=O)=C1)O UQCIMMPORGZRJA-UHFFFAOYSA-N 0.000 claims 1
- AHOZSTCYNZBZFF-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OC)=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OC)=CC(S(C)(=O)=O)=C1)O AHOZSTCYNZBZFF-UHFFFAOYSA-N 0.000 claims 1
- RJSKRNSVSDHNGN-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OC2CC2)=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OC2CC2)=CC(S(C)(=O)=O)=C1)O RJSKRNSVSDHNGN-UHFFFAOYSA-N 0.000 claims 1
- GOYJGDQWAPDLLF-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OCC2CC2)=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OCC2CC2)=CC(S(C)(=O)=O)=C1)O GOYJGDQWAPDLLF-UHFFFAOYSA-N 0.000 claims 1
- IKRFRXWLZBPDLP-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OCCOC)=CC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OCCOC)=CC(S(C)(=O)=O)=C1)O IKRFRXWLZBPDLP-UHFFFAOYSA-N 0.000 claims 1
- NCKIILZPZSRBKS-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C1)O NCKIILZPZSRBKS-UHFFFAOYSA-N 0.000 claims 1
- LGUSQELLYROSPQ-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(S(C)(=O)=O)=CC(OC(F)(F)F)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(S(C)(=O)=O)=CC(OC(F)(F)F)=C1)O LGUSQELLYROSPQ-UHFFFAOYSA-N 0.000 claims 1
- CRYYNUKAFOYAMC-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(S(C)(=O)=O)=CC=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(S(C)(=O)=O)=CC=C1)O CRYYNUKAFOYAMC-UHFFFAOYSA-N 0.000 claims 1
- JFNYVTUPDNRKHJ-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C#N)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C#N)=C1)O JFNYVTUPDNRKHJ-UHFFFAOYSA-N 0.000 claims 1
- CRYJRZNRCYWPDX-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1)N Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1)N CRYJRZNRCYWPDX-UHFFFAOYSA-N 0.000 claims 1
- YWPUIDVLPXLPKH-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1)O YWPUIDVLPXLPKH-UHFFFAOYSA-N 0.000 claims 1
- NHPFNSXLPNCKJP-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2CCOCC2)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2CCOCC2)=C1)O NHPFNSXLPNCKJP-UHFFFAOYSA-N 0.000 claims 1
- VUGYIZUZERLVLO-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(COC)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(COC)=C1)O VUGYIZUZERLVLO-UHFFFAOYSA-N 0.000 claims 1
- VFGFKAPQKZROLK-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OC(C2)CC2OC)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OC(C2)CC2OC)=C1)O VFGFKAPQKZROLK-UHFFFAOYSA-N 0.000 claims 1
- HXQVZOBVKQEION-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OC)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OC)=C1)O HXQVZOBVKQEION-UHFFFAOYSA-N 0.000 claims 1
- ASAYZXROFMJHIY-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OC2CCC2)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OC2CCC2)=C1)O ASAYZXROFMJHIY-UHFFFAOYSA-N 0.000 claims 1
- GPOPLYHJFHGUEF-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OC2COC2)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OC2COC2)=C1)O GPOPLYHJFHGUEF-UHFFFAOYSA-N 0.000 claims 1
- JXYZDYVCIPUKPV-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2CC2)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2CC2)=C1)O JXYZDYVCIPUKPV-UHFFFAOYSA-N 0.000 claims 1
- PGHGPLBYPOKDJQ-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2COC2)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2COC2)=C1)O PGHGPLBYPOKDJQ-UHFFFAOYSA-N 0.000 claims 1
- JISHIWRFEGNTMH-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCCO)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCCO)=C1)O JISHIWRFEGNTMH-UHFFFAOYSA-N 0.000 claims 1
- LDKAHJQVLNJWOF-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCCOC)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCCOC)=C1)O LDKAHJQVLNJWOF-UHFFFAOYSA-N 0.000 claims 1
- DCZXTSIGKYHACG-CALCHBBNSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(O[C@H](C2)C[C@H]2O)=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(O[C@H](C2)C[C@H]2O)=C1)O DCZXTSIGKYHACG-CALCHBBNSA-N 0.000 claims 1
- OQLIDGJZDIEERS-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC2=C1OCCO2)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC2=C1OCCO2)O OQLIDGJZDIEERS-UHFFFAOYSA-N 0.000 claims 1
- GHXNOSFNVKAWDP-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC=C1)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC=C1)O GHXNOSFNVKAWDP-UHFFFAOYSA-N 0.000 claims 1
- NPGQJKPXMOWWTM-UHFFFAOYSA-N CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC=C1C)O Chemical compound CC(C)(C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC=C1C)O NPGQJKPXMOWWTM-UHFFFAOYSA-N 0.000 claims 1
- OGCBBWZJEMNGQZ-UHFFFAOYSA-N CC(C)(C(C=CN=C1)=C1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C(C=CN=C1)=C1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)O OGCBBWZJEMNGQZ-UHFFFAOYSA-N 0.000 claims 1
- DSFNNWYFUFXEED-UHFFFAOYSA-N CC(C)(C(N1)=O)OC(C=C2)=C1N=C2C(C(NC1=NC(S(C)(=O)=O)=CC(C)=C1)=C1)=CN=C1NC(C)=O Chemical compound CC(C)(C(N1)=O)OC(C=C2)=C1N=C2C(C(NC1=NC(S(C)(=O)=O)=CC(C)=C1)=C1)=CN=C1NC(C)=O DSFNNWYFUFXEED-UHFFFAOYSA-N 0.000 claims 1
- JYOMZSHESGXMQT-UHFFFAOYSA-N CC(C)(C1)OC(C)(C)CC1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)(C1)OC(C)(C)CC1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 JYOMZSHESGXMQT-UHFFFAOYSA-N 0.000 claims 1
- RALMXJBXLIZDJK-UHFFFAOYSA-N CC(C)(C1)OCCN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC=C1 Chemical compound CC(C)(C1)OCCN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC=C1 RALMXJBXLIZDJK-UHFFFAOYSA-N 0.000 claims 1
- CXGFYRJRNMSIAR-UHFFFAOYSA-N CC(C)(C1=CC(C(C=NC(NC(C)=O)=C2)=C2NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1)O Chemical compound CC(C)(C1=CC(C(C=NC(NC(C)=O)=C2)=C2NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1)O CXGFYRJRNMSIAR-UHFFFAOYSA-N 0.000 claims 1
- GMQIHVFBEKCPNZ-UHFFFAOYSA-N CC(C)(C1=CC(C(C=NC(NC(C)=O)=C2)=C2NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1)O Chemical compound CC(C)(C1=CC(C(C=NC(NC(C)=O)=C2)=C2NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1)O GMQIHVFBEKCPNZ-UHFFFAOYSA-N 0.000 claims 1
- FVICFEFDAYCEML-UHFFFAOYSA-N CC(C)(C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)O FVICFEFDAYCEML-UHFFFAOYSA-N 0.000 claims 1
- VVPDMBOQVMIQIX-UHFFFAOYSA-N CC(C)(C1=COC(C(C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C2)=CN=C2NC(C)=O)=C1)O Chemical compound CC(C)(C1=COC(C(C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C2)=CN=C2NC(C)=O)=C1)O VVPDMBOQVMIQIX-UHFFFAOYSA-N 0.000 claims 1
- UBTIKUANLDBEQK-UHFFFAOYSA-N CC(C)(CO)COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)(CO)COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1 UBTIKUANLDBEQK-UHFFFAOYSA-N 0.000 claims 1
- RIKOZEKUSRNIOD-UHFFFAOYSA-N CC(C)(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)N1CCOCC1 Chemical compound CC(C)(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)N1CCOCC1 RIKOZEKUSRNIOD-UHFFFAOYSA-N 0.000 claims 1
- ZRPPWNFYNOVMNF-UHFFFAOYSA-N CC(C)(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)O ZRPPWNFYNOVMNF-UHFFFAOYSA-N 0.000 claims 1
- UWUCMPTYYGVMCY-UHFFFAOYSA-N CC(C)(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)OC Chemical compound CC(C)(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)OC UWUCMPTYYGVMCY-UHFFFAOYSA-N 0.000 claims 1
- JPYKJIDLISYYAK-UHFFFAOYSA-N CC(C)(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(C)(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)O JPYKJIDLISYYAK-UHFFFAOYSA-N 0.000 claims 1
- PTQBDVYSRFVTBD-UHFFFAOYSA-N CC(C)(COCC1)N1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)(COCC1)N1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 PTQBDVYSRFVTBD-UHFFFAOYSA-N 0.000 claims 1
- MEJZPWKEEWWYGN-UHFFFAOYSA-N CC(C)C(C=CN=C1)=C1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)C(C=CN=C1)=C1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 MEJZPWKEEWWYGN-UHFFFAOYSA-N 0.000 claims 1
- TXPKONQDTBNNHC-UHFFFAOYSA-N CC(C)COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1 TXPKONQDTBNNHC-UHFFFAOYSA-N 0.000 claims 1
- GBTCWBDMJKJKGN-UHFFFAOYSA-N CC(C)COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1 GBTCWBDMJKJKGN-UHFFFAOYSA-N 0.000 claims 1
- HETMMYNZKOXAID-UHFFFAOYSA-N CC(C)N(C=C1)N=C1C(C(NC1=CC(OC(C)C)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O Chemical compound CC(C)N(C=C1)N=C1C(C(NC1=CC(OC(C)C)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O HETMMYNZKOXAID-UHFFFAOYSA-N 0.000 claims 1
- FRSXNPBULDHJLQ-UHFFFAOYSA-N CC(C)N(C=C1)N=C1C(C(NC1=CC(OC)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O Chemical compound CC(C)N(C=C1)N=C1C(C(NC1=CC(OC)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O FRSXNPBULDHJLQ-UHFFFAOYSA-N 0.000 claims 1
- IJRSSZJTFIJSRK-UHFFFAOYSA-N CC(C)N(C=C1)N=C1C(C(NC1=CC(OCCO)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O Chemical compound CC(C)N(C=C1)N=C1C(C(NC1=CC(OCCO)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O IJRSSZJTFIJSRK-UHFFFAOYSA-N 0.000 claims 1
- HHSZQQYBYUMGPO-UHFFFAOYSA-N CC(C)N(C=C1)N=C1C(C(NC1=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C1)=C1)=CN=C1NC(C)=O Chemical compound CC(C)N(C=C1)N=C1C(C(NC1=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C1)=C1)=CN=C1NC(C)=O HHSZQQYBYUMGPO-UHFFFAOYSA-N 0.000 claims 1
- ZGFUWHRJEOEVSB-UHFFFAOYSA-N CC(C)N(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OC(C)C)=C1)=C1)=CN=C1NC(C)=O Chemical compound CC(C)N(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OC(C)C)=C1)=C1)=CN=C1NC(C)=O ZGFUWHRJEOEVSB-UHFFFAOYSA-N 0.000 claims 1
- HQCCGKFZXMQVJG-UHFFFAOYSA-N CC(C)N(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OCCO)=C1)=C1)=CN=C1NC(C)=O Chemical compound CC(C)N(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OCCO)=C1)=C1)=CN=C1NC(C)=O HQCCGKFZXMQVJG-UHFFFAOYSA-N 0.000 claims 1
- CDFYPXXRHLZQGE-UHFFFAOYSA-N CC(C)N(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OCCOC)=C1)=C1)=CN=C1NC(C)=O Chemical compound CC(C)N(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OCCOC)=C1)=C1)=CN=C1NC(C)=O CDFYPXXRHLZQGE-UHFFFAOYSA-N 0.000 claims 1
- HKBXSTDBDJGFSK-UHFFFAOYSA-N CC(C)N(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC=C1)=C1)=CN=C1NC(C)=O Chemical compound CC(C)N(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC=C1)=C1)=CN=C1NC(C)=O HKBXSTDBDJGFSK-UHFFFAOYSA-N 0.000 claims 1
- BJWNNUNJSJUFNV-UHFFFAOYSA-N CC(C)OC(C(NC1=CC(NC(C)=O)=NC=C1C1=NN(C)C=C1)=N1)=CC=C1S(C)(=O)=O Chemical compound CC(C)OC(C(NC1=CC(NC(C)=O)=NC=C1C1=NN(C)C=C1)=N1)=CC=C1S(C)(=O)=O BJWNNUNJSJUFNV-UHFFFAOYSA-N 0.000 claims 1
- MTENUSGRKQHQPT-UHFFFAOYSA-N CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2C#N)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2C#N)=NC(S(C)(=O)=O)=C1 MTENUSGRKQHQPT-UHFFFAOYSA-N 0.000 claims 1
- CFDYMGHINVDQHD-UHFFFAOYSA-N CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2F)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2F)=NC(S(C)(=O)=O)=C1 CFDYMGHINVDQHD-UHFFFAOYSA-N 0.000 claims 1
- QSRWAPQFTILFOR-UHFFFAOYSA-N CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C(C3)COC3C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C(C3)COC3C2)=NC(S(C)(=O)=O)=C1 QSRWAPQFTILFOR-UHFFFAOYSA-N 0.000 claims 1
- DBTIJWTWNRVQJY-UHFFFAOYSA-N CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2CC(COC)OCC2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2CC(COC)OCC2)=NC(S(C)(=O)=O)=C1 DBTIJWTWNRVQJY-UHFFFAOYSA-N 0.000 claims 1
- SPMVIRLEPSXYSV-HDICACEKSA-N CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1 SPMVIRLEPSXYSV-HDICACEKSA-N 0.000 claims 1
- MDRORRMRUANQDH-UHFFFAOYSA-N CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2OCCOC)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2OCCOC)=NC(S(C)(=O)=O)=C1 MDRORRMRUANQDH-UHFFFAOYSA-N 0.000 claims 1
- GOZVHVAHSFWKBV-UHFFFAOYSA-N CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC(C#N)=CC=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC(C#N)=CC=C2)=NC(S(C)(=O)=O)=C1 GOZVHVAHSFWKBV-UHFFFAOYSA-N 0.000 claims 1
- GOKHBRKQXPDIFM-UHFFFAOYSA-N CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1 GOKHBRKQXPDIFM-UHFFFAOYSA-N 0.000 claims 1
- BJHCGHNPPVXCPF-UHFFFAOYSA-N CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(F)(F)F)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(F)(F)F)C=C2)=NC(S(C)(=O)=O)=C1 BJHCGHNPPVXCPF-UHFFFAOYSA-N 0.000 claims 1
- LHBWAMLLIORHFE-UHFFFAOYSA-N CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(COC)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(COC)C=C2)=NC(S(C)(=O)=O)=C1 LHBWAMLLIORHFE-UHFFFAOYSA-N 0.000 claims 1
- IKXOJUQXLZIMDR-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C(C=C2)=NC3=C2OCCN3C(C)=O)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C(C=C2)=NC3=C2OCCN3C(C)=O)=NC(S(C)(=O)=O)=C1 IKXOJUQXLZIMDR-UHFFFAOYSA-N 0.000 claims 1
- GHIVTUUNUOFONI-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C(C=C2)=NN3C2=NC=C3)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C(C=C2)=NN3C2=NC=C3)=NC(S(C)(=O)=O)=C1 GHIVTUUNUOFONI-UHFFFAOYSA-N 0.000 claims 1
- BNYKKLSGNRTCFM-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C(N=C2)=CC3=C2NCCO3)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C(N=C2)=CC3=C2NCCO3)=NC(S(C)(=O)=O)=C1 BNYKKLSGNRTCFM-UHFFFAOYSA-N 0.000 claims 1
- INHVLXDKGCCKIP-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCCOC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCCOC3=N2)=NC(S(C)(=O)=O)=C1 INHVLXDKGCCKIP-UHFFFAOYSA-N 0.000 claims 1
- XECIHCAWBBMTGJ-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCOC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCOC3=N2)=NC(S(C)(=O)=O)=C1 XECIHCAWBBMTGJ-UHFFFAOYSA-N 0.000 claims 1
- JQLRLBVFVLRVKK-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CNC=N2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CNC=N2)=NC(S(C)(=O)=O)=C1 JQLRLBVFVLRVKK-UHFFFAOYSA-N 0.000 claims 1
- KDOKHPNNQXYSQH-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C(C)=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C(C)=C2)=NC(S(C)(=O)=O)=C1 KDOKHPNNQXYSQH-UHFFFAOYSA-N 0.000 claims 1
- MGVMEUNTXYVWPZ-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C3C2COCC3)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C3C2COCC3)=NC(S(C)(=O)=O)=C1 MGVMEUNTXYVWPZ-UHFFFAOYSA-N 0.000 claims 1
- BBGDAJPXQQLXRI-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1 BBGDAJPXQQLXRI-UHFFFAOYSA-N 0.000 claims 1
- FUVGPTKYHVEKKT-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C3CC3)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C3CC3)C=C2)=NC(S(C)(=O)=O)=C1 FUVGPTKYHVEKKT-UHFFFAOYSA-N 0.000 claims 1
- MMOAYEWTUCYPHR-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C3CCC3)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C3CCC3)C=C2)=NC(S(C)(=O)=O)=C1 MMOAYEWTUCYPHR-UHFFFAOYSA-N 0.000 claims 1
- VDALGKGTLYIFQE-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(CCN(C)C3)C3=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(CCN(C)C3)C3=C2)=NC(S(C)(=O)=O)=C1 VDALGKGTLYIFQE-UHFFFAOYSA-N 0.000 claims 1
- JHHCJEUFEQVOSQ-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(CCO)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(CCO)C=C2)=NC(S(C)(=O)=O)=C1 JHHCJEUFEQVOSQ-UHFFFAOYSA-N 0.000 claims 1
- YOSOKELCOIOHDD-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(CCOC3)C3=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(CCOC3)C3=C2)=NC(S(C)(=O)=O)=C1 YOSOKELCOIOHDD-UHFFFAOYSA-N 0.000 claims 1
- RTXBNHLLIGZBMS-INIZCTEOSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN([C@@H]3COCC3)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN([C@@H]3COCC3)C=C2)=NC(S(C)(=O)=O)=C1 RTXBNHLLIGZBMS-INIZCTEOSA-N 0.000 claims 1
- RTXBNHLLIGZBMS-MRXNPFEDSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN([C@H]3COCC3)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN([C@H]3COCC3)C=C2)=NC(S(C)(=O)=O)=C1 RTXBNHLLIGZBMS-MRXNPFEDSA-N 0.000 claims 1
- ILTIKAHKYPZJQG-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2N2C=NC=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2N2C=NC=C2)=NC(S(C)(=O)=O)=C1 ILTIKAHKYPZJQG-UHFFFAOYSA-N 0.000 claims 1
- FSKNPLRAEUBFLI-UHFFFAOYSA-N CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2N2N=CC=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2N2N=CC=C2)=NC(S(C)(=O)=O)=C1 FSKNPLRAEUBFLI-UHFFFAOYSA-N 0.000 claims 1
- KOQNEINRMWAWHN-UHFFFAOYSA-N CC(C)OC1=CC(S(C)(=O)=O)=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2F)=C1 Chemical compound CC(C)OC1=CC(S(C)(=O)=O)=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2F)=C1 KOQNEINRMWAWHN-UHFFFAOYSA-N 0.000 claims 1
- XHTGFYIGKSMLRU-UHFFFAOYSA-N CC(C)OC1=CC=C(C(C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C2)=CN=C2NC(C)=O)N=N1 Chemical compound CC(C)OC1=CC=C(C(C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C2)=CN=C2NC(C)=O)N=N1 XHTGFYIGKSMLRU-UHFFFAOYSA-N 0.000 claims 1
- MKAPVMYGHAFGBU-UHFFFAOYSA-N CC(C)OC1=CC=C(C(C(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C2)=CN=C2NC(C)=O)N=N1 Chemical compound CC(C)OC1=CC=C(C(C(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C2)=CN=C2NC(C)=O)N=N1 MKAPVMYGHAFGBU-UHFFFAOYSA-N 0.000 claims 1
- NQTVZFQSHFWMFS-UHFFFAOYSA-N CC(C)S(C1=CC=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=N1)(=O)=O Chemical compound CC(C)S(C1=CC=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=N1)(=O)=O NQTVZFQSHFWMFS-UHFFFAOYSA-N 0.000 claims 1
- MBACNRFTXBWMEG-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC(N=C12)=CC=C1OCCCS2(=O)=O Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC(N=C12)=CC=C1OCCCS2(=O)=O MBACNRFTXBWMEG-UHFFFAOYSA-N 0.000 claims 1
- MKYHFRJWMAIHIH-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OCCC2)=C2C(S(C)(=O)=O)=N1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OCCC2)=C2C(S(C)(=O)=O)=N1 MKYHFRJWMAIHIH-UHFFFAOYSA-N 0.000 claims 1
- ZCIIPACPWWMZGQ-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC=C(CCCS2(=O)=O)C2=N1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC=C(CCCS2(=O)=O)C2=N1 ZCIIPACPWWMZGQ-UHFFFAOYSA-N 0.000 claims 1
- INLYRJAKZOJSMG-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C(C)(C)O)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C(C)(C)O)=C1 INLYRJAKZOJSMG-UHFFFAOYSA-N 0.000 claims 1
- BECWKZLEOXFMRD-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2(CC2)O)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2(CC2)O)=C1 BECWKZLEOXFMRD-UHFFFAOYSA-N 0.000 claims 1
- WQYYFXVQSWAPRH-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2(CO)COCC2)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2(CO)COCC2)=C1 WQYYFXVQSWAPRH-UHFFFAOYSA-N 0.000 claims 1
- VLOKQTAGZBZSBW-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2(COCC2)O)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2(COCC2)O)=C1 VLOKQTAGZBZSBW-UHFFFAOYSA-N 0.000 claims 1
- XESUKBAKWWVIFD-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2(COCC2)OC)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2(COCC2)OC)=C1 XESUKBAKWWVIFD-UHFFFAOYSA-N 0.000 claims 1
- HIDOVVAKJOSIOW-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2=NN(C)C=C2)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2=NN(C)C=C2)=C1 HIDOVVAKJOSIOW-UHFFFAOYSA-N 0.000 claims 1
- HMCBRRNWDCITSS-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2COCC2)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C2COCC2)=C1 HMCBRRNWDCITSS-UHFFFAOYSA-N 0.000 claims 1
- XDMYFNUSDMUUAW-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(COC2COCC2)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(COC2COCC2)=C1 XDMYFNUSDMUUAW-UHFFFAOYSA-N 0.000 claims 1
- WVNPDDPQGRQIKX-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(N2CCOCC2)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(N2CCOCC2)=C1 WVNPDDPQGRQIKX-UHFFFAOYSA-N 0.000 claims 1
- XNLDSOWRNDRVFX-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC(C)(C)CO)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC(C)(C)CO)=C1 XNLDSOWRNDRVFX-UHFFFAOYSA-N 0.000 claims 1
- WPXYWPXEUBRRBF-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC(C)(C)O)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC(C)(C)O)=C1 WPXYWPXEUBRRBF-UHFFFAOYSA-N 0.000 claims 1
- LJDHSOGTOAESLL-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2(CC2)O)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2(CC2)O)=C1 LJDHSOGTOAESLL-UHFFFAOYSA-N 0.000 claims 1
- BLZZFFLUEJLANT-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2(CC2)OC)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2(CC2)OC)=C1 BLZZFFLUEJLANT-UHFFFAOYSA-N 0.000 claims 1
- XZOQZYFFTRGZGU-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2COCC2)=C1 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2COCC2)=C1 XZOQZYFFTRGZGU-UHFFFAOYSA-N 0.000 claims 1
- FUAMUZIVZDYMTG-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC2=C1CCCO2 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC2=C1CCCO2 FUAMUZIVZDYMTG-UHFFFAOYSA-N 0.000 claims 1
- AAXVKSHISNXFOE-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC2=C1OCO2 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC2=C1OCO2 AAXVKSHISNXFOE-UHFFFAOYSA-N 0.000 claims 1
- OCQWCZQZCSOENQ-UHFFFAOYSA-N CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CN2C1=NC=C2 Chemical compound CC(C1)OC(C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CN2C1=NC=C2 OCQWCZQZCSOENQ-UHFFFAOYSA-N 0.000 claims 1
- SOMMLODVMNAEIX-UHFFFAOYSA-N CC(C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)OC Chemical compound CC(C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)OC SOMMLODVMNAEIX-UHFFFAOYSA-N 0.000 claims 1
- MSHDOAMGOZVSFA-UHFFFAOYSA-N CC(CC1)(CN1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(CC1)(CN1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1)O MSHDOAMGOZVSFA-UHFFFAOYSA-N 0.000 claims 1
- CKAZNYUENUHUNM-UHFFFAOYSA-N CC(COC(C)C1)N1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1 Chemical compound CC(COC(C)C1)N1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1 CKAZNYUENUHUNM-UHFFFAOYSA-N 0.000 claims 1
- STKIHWLOFWZPOS-UHFFFAOYSA-N CC(COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1)O STKIHWLOFWZPOS-UHFFFAOYSA-N 0.000 claims 1
- ZEHIDSBKMACQTO-UHFFFAOYSA-N CC(COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1)OC Chemical compound CC(COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1)OC ZEHIDSBKMACQTO-UHFFFAOYSA-N 0.000 claims 1
- NDHALVUEHYNDEA-UHFFFAOYSA-N CC(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C(N3CCOCC3)=C2)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C(N3CCOCC3)=C2)=NC(S(C)(=O)=O)=C1)O NDHALVUEHYNDEA-UHFFFAOYSA-N 0.000 claims 1
- YCPIUTSURRDLIE-UHFFFAOYSA-N CC(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)O YCPIUTSURRDLIE-UHFFFAOYSA-N 0.000 claims 1
- RNTVRCXLFIJIPL-UHFFFAOYSA-N CC(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)OC Chemical compound CC(COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)OC RNTVRCXLFIJIPL-UHFFFAOYSA-N 0.000 claims 1
- AXIYDTAJFSEZED-UHFFFAOYSA-N CC(NC(C=C1NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1C1=NC(C)=NC(C)=C1)=O Chemical compound CC(NC(C=C1NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1C1=NC(C)=NC(C)=C1)=O AXIYDTAJFSEZED-UHFFFAOYSA-N 0.000 claims 1
- RWGZKPGJVPZBAL-UHFFFAOYSA-N CC(NC(C=C1NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1C1=NC=C(C)N=C1)=O Chemical compound CC(NC(C=C1NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1C1=NC=C(C)N=C1)=O RWGZKPGJVPZBAL-UHFFFAOYSA-N 0.000 claims 1
- PCFROIQVTXUZCV-UHFFFAOYSA-N CC(NC(C=C1NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1C1=NC=CN=C1)=O Chemical compound CC(NC(C=C1NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1C1=NC=CN=C1)=O PCFROIQVTXUZCV-UHFFFAOYSA-N 0.000 claims 1
- RQBYMCWSPNDDML-UHFFFAOYSA-N CC(NC(C=C1NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1N(CCC1)C1=O)=O Chemical compound CC(NC(C=C1NC2=CC(S(C)(=O)=O)=CC=C2)=NC=C1N(CCC1)C1=O)=O RQBYMCWSPNDDML-UHFFFAOYSA-N 0.000 claims 1
- XAEPBBLBNHTYQC-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C(C=C1)=NN2C1=CN=C2)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C(C=C1)=NN2C1=CN=C2)=O XAEPBBLBNHTYQC-UHFFFAOYSA-N 0.000 claims 1
- AEUVETDVNFGMOY-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C(C=C1)=NN2C1=NC=C2)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C(C=C1)=NN2C1=NC=C2)=O AEUVETDVNFGMOY-UHFFFAOYSA-N 0.000 claims 1
- HMPUIALERVBWAI-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C(N=C1)=CC2=C1OCCO2)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C(N=C1)=CC2=C1OCCO2)=O HMPUIALERVBWAI-UHFFFAOYSA-N 0.000 claims 1
- MUTVZCYPKJBWPB-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C(N=C1)=CC2=C1OCO2)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C(N=C1)=CC2=C1OCO2)=O MUTVZCYPKJBWPB-UHFFFAOYSA-N 0.000 claims 1
- PIWKKYAAAURRGF-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C(N=C1S2)=CC=C1N1C2=NC=C1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C(N=C1S2)=CC=C1N1C2=NC=C1)=O PIWKKYAAAURRGF-UHFFFAOYSA-N 0.000 claims 1
- TZMADQZMHIXPCK-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C1=CC=C(C2=C(CO3)C=NN2C)C3=N1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C1=CC=C(C2=C(CO3)C=NN2C)C3=N1)=O TZMADQZMHIXPCK-UHFFFAOYSA-N 0.000 claims 1
- ZRSJFHALYRJQKJ-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C1=CC=C2OCCOC2=N1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C1=CC=C2OCCOC2=N1)=O ZRSJFHALYRJQKJ-UHFFFAOYSA-N 0.000 claims 1
- KNOSPSBQSCVSDK-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C1=NC2=CC=NN2C=C1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C1=NC2=CC=NN2C=C1)=O KNOSPSBQSCVSDK-UHFFFAOYSA-N 0.000 claims 1
- QZTSPHPQLLZQQN-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C1=NC=CC2=C1OCO2)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1C1=NC=CC2=C1OCO2)=O QZTSPHPQLLZQQN-UHFFFAOYSA-N 0.000 claims 1
- NIVCZHVCGBGDGS-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1OC1=NC=CC=C1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C)=C2)=NC=C1OC1=NC=CC=C1)=O NIVCZHVCGBGDGS-UHFFFAOYSA-N 0.000 claims 1
- MRVYTTVWZATHHD-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1C(C=C1)=NNC1=O)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1C(C=C1)=NNC1=O)=O MRVYTTVWZATHHD-UHFFFAOYSA-N 0.000 claims 1
- DXKGNJLHAQALBB-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1C(N=C1S2)=CC=C1N1C2=NC=C1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1C(N=C1S2)=CC=C1N1C2=NC=C1)=O DXKGNJLHAQALBB-UHFFFAOYSA-N 0.000 claims 1
- CNCYSUOCJLWHLD-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1C1=CC=C(C2=C(CO3)C=NN2C)C3=N1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1C1=CC=C(C2=C(CO3)C=NN2C)C3=N1)=O CNCYSUOCJLWHLD-UHFFFAOYSA-N 0.000 claims 1
- KESFVFJJVNVCOX-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1N1N=C(CCN(C)C2=CC=C3)C2=C3C1=O)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1N1N=C(CCN(C)C2=CC=C3)C2=C3C1=O)=O KESFVFJJVNVCOX-UHFFFAOYSA-N 0.000 claims 1
- CZJJXFONJSDWPJ-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1N1N=C(CCOC2=CC=C3)C2=C3C1=O)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1N1N=C(CCOC2=CC=C3)C2=C3C1=O)=O CZJJXFONJSDWPJ-UHFFFAOYSA-N 0.000 claims 1
- RPBJCVYYLXZHLA-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1N1N=CC=CC1=O)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=NC=C1N1N=CC=CC1=O)=O RPBJCVYYLXZHLA-UHFFFAOYSA-N 0.000 claims 1
- YGFKXASXWHURIK-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3=NN(C)C=C3)=C2)=NC=C1OCC1(CC1)O)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3=NN(C)C=C3)=C2)=NC=C1OCC1(CC1)O)=O YGFKXASXWHURIK-UHFFFAOYSA-N 0.000 claims 1
- AUUPHJKLFYHAQP-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3=NN(C)C=C3)=C2)=NC=C1OCC1CC1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(C3=NN(C)C=C3)=C2)=NC=C1OCC1CC1)=O AUUPHJKLFYHAQP-UHFFFAOYSA-N 0.000 claims 1
- ZDXQONPEDARCJO-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=NC=C1C(N=C1)=CC2=C1OCCO2)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=NC=C1C(N=C1)=CC2=C1OCCO2)=O ZDXQONPEDARCJO-UHFFFAOYSA-N 0.000 claims 1
- SUGWMSLDSJNFRP-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=NC=C1C1=CC=C2OCCOC2=N1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=NC=C1C1=CC=C2OCCOC2=N1)=O SUGWMSLDSJNFRP-UHFFFAOYSA-N 0.000 claims 1
- SPMZYOVMPMRETC-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=NC=C1C1=CC=C2OCOC2=N1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=NC=C1C1=CC=C2OCOC2=N1)=O SPMZYOVMPMRETC-UHFFFAOYSA-N 0.000 claims 1
- JSEMOBMYNJNZSA-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=NC=C1C1=CC=C2OCOC2=N1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=NC=C1C1=CC=C2OCOC2=N1)=O JSEMOBMYNJNZSA-UHFFFAOYSA-N 0.000 claims 1
- OKGWWQAJFOHNPE-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=NC=C1C1=NC2=CC=NN2C=C1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=NC=C1C1=NC2=CC=NN2C=C1)=O OKGWWQAJFOHNPE-UHFFFAOYSA-N 0.000 claims 1
- WRFHZNDYTJCPLD-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC3=C2OCO3)=NC=C1C(N=N1)=CC=C1OC)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC3=C2OCO3)=NC=C1C(N=N1)=CC=C1OC)=O WRFHZNDYTJCPLD-UHFFFAOYSA-N 0.000 claims 1
- COMLSDCELHEMME-UHFFFAOYSA-N CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC=C2)=NC=C1C1=CC=CN=N1)=O Chemical compound CC(NC(C=C1NC2=NC(S(C)(=O)=O)=CC=C2)=NC=C1C1=CC=CN=N1)=O COMLSDCELHEMME-UHFFFAOYSA-N 0.000 claims 1
- MSNAYLQHRCSOJZ-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC(C=CC=C2)=C2S(C)(=O)=O)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(NC(C=CC=C2)=C2S(C)(=O)=O)=C1C1=NC=CC=C1)=O MSNAYLQHRCSOJZ-UHFFFAOYSA-N 0.000 claims 1
- MSGJPDKCYDYYGK-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC(N=C23)=CC=C2OCCS3(=O)=O)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(NC(N=C23)=CC=C2OCCS3(=O)=O)=C1C1=NC=CC=C1)=O MSGJPDKCYDYYGK-UHFFFAOYSA-N 0.000 claims 1
- YDRBUNKZUMEXGG-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(C#N)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(C#N)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O YDRBUNKZUMEXGG-UHFFFAOYSA-N 0.000 claims 1
- OHKABRVOULVBMZ-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(C)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(C)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O OHKABRVOULVBMZ-UHFFFAOYSA-N 0.000 claims 1
- WTJHHJLSKVOZBL-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(OC)=CC=C2)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(OC)=CC=C2)=C1C1=NC=CC=C1)=O WTJHHJLSKVOZBL-UHFFFAOYSA-N 0.000 claims 1
- ZVTLXUKHULWHOB-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(OCC3CC3)=CC(S(C)(=O)=O)=C2)=C1C(C=C1)=NC=C1OCCOC)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(OCC3CC3)=CC(S(C)(=O)=O)=C2)=C1C(C=C1)=NC=C1OCCOC)=O ZVTLXUKHULWHOB-UHFFFAOYSA-N 0.000 claims 1
- HTSYEQMXMWQPNH-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(OCC3CC3)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(OCC3CC3)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O HTSYEQMXMWQPNH-UHFFFAOYSA-N 0.000 claims 1
- DEMDTWBGYGBATJ-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(OCCO)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(OCCO)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O DEMDTWBGYGBATJ-UHFFFAOYSA-N 0.000 claims 1
- GRYVGAGDAHHURY-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(OCCOC)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(OCCOC)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O GRYVGAGDAHHURY-UHFFFAOYSA-N 0.000 claims 1
- DHTJHPVTUDVSFQ-SAABIXHNSA-N CC(NC(N=C1)=CC(NC2=CC(O[C@H](C3)C[C@@H]3O)=CC(S(C)(=O)=O)=C2)=C1C(C=C1)=NC=C1F)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(O[C@H](C3)C[C@@H]3O)=CC(S(C)(=O)=O)=C2)=C1C(C=C1)=NC=C1F)=O DHTJHPVTUDVSFQ-SAABIXHNSA-N 0.000 claims 1
- PZMNLSCDJOHFQP-SAABIXHNSA-N CC(NC(N=C1)=CC(NC2=CC(O[C@H](C3)C[C@@H]3O)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(O[C@H](C3)C[C@@H]3O)=CC(S(C)(=O)=O)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O PZMNLSCDJOHFQP-SAABIXHNSA-N 0.000 claims 1
- CZRBNCKRCBDZLV-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C2)=C1C(C=C1)=NC=C1F)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C2)=C1C(C=C1)=NC=C1F)=O CZRBNCKRCBDZLV-UHFFFAOYSA-N 0.000 claims 1
- IPJWJLUUQIGJAK-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C2)=C1C(C=C1)=NC=C1OCCOC)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C2)=C1C(C=C1)=NC=C1OCCOC)=O IPJWJLUUQIGJAK-UHFFFAOYSA-N 0.000 claims 1
- OUPPWUPKSTXBNA-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1N1CCOCC1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1N1CCOCC1)=O OUPPWUPKSTXBNA-UHFFFAOYSA-N 0.000 claims 1
- NPJSPPMJBCMZJN-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1OCCOC)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1OCCOC)=O NPJSPPMJBCMZJN-UHFFFAOYSA-N 0.000 claims 1
- FESQFZHJPOQTRU-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC(S(C)(=O)=O)=CC=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O FESQFZHJPOQTRU-UHFFFAOYSA-N 0.000 claims 1
- CPXCOUDOJMXUEN-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=CC=CC=C2)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=CC=CC=C2)=C1C1=NC=CC=C1)=O CPXCOUDOJMXUEN-UHFFFAOYSA-N 0.000 claims 1
- SODXCJXHDLJBPY-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C(C=C1)=NC=C1N1CC(CC2)OC2C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C(C=C1)=NC=C1N1CC(CC2)OC2C1)=O SODXCJXHDLJBPY-UHFFFAOYSA-N 0.000 claims 1
- GRANATCGBFZLLW-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C(C=C1)=NC=C1OCCOC)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C(C=C1)=NC=C1OCCOC)=O GRANATCGBFZLLW-UHFFFAOYSA-N 0.000 claims 1
- AKFGIUJOTPPNNJ-KRWDZBQOSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C(C=C1)=NC=C1O[C@@H]1COCC1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C(C=C1)=NC=C1O[C@@H]1COCC1)=O AKFGIUJOTPPNNJ-KRWDZBQOSA-N 0.000 claims 1
- BKVBCJAEKUBNNE-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C1=NC=C(COC)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1C1=NC=C(COC)C=C1)=O BKVBCJAEKUBNNE-UHFFFAOYSA-N 0.000 claims 1
- IBLKZJHJASHPOC-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1C(C=C1)=NC=C1N(CC1=CC=CC=C11)C1=O)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1C(C=C1)=NC=C1N(CC1=CC=CC=C11)C1=O)=O IBLKZJHJASHPOC-UHFFFAOYSA-N 0.000 claims 1
- AEBGMHNRRMDKNL-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(COC)=C2)=C1C1=NC=C(COC)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(COC)=C2)=C1C1=NC=C(COC)C=C1)=O AEBGMHNRRMDKNL-UHFFFAOYSA-N 0.000 claims 1
- SLXIKJZIZZZDEY-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1C(C=C1)=NC=C1OCCOC)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1C(C=C1)=NC=C1OCCOC)=O SLXIKJZIZZZDEY-UHFFFAOYSA-N 0.000 claims 1
- WVFDZLJCIWQXMP-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O WVFDZLJCIWQXMP-UHFFFAOYSA-N 0.000 claims 1
- NRJXBSFSSYKPDT-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1C1=NC=C(COC)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1C1=NC=C(COC)C=C1)=O NRJXBSFSSYKPDT-UHFFFAOYSA-N 0.000 claims 1
- OYWUDCJBTSWDCY-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCC3CC3)=C2)=C1C(C=C1)=NC=C1OCCOC)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCC3CC3)=C2)=C1C(C=C1)=NC=C1OCCOC)=O OYWUDCJBTSWDCY-UHFFFAOYSA-N 0.000 claims 1
- RIXFJPPIZZGLJO-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1C(C=C1)=NC=C1N(CCOC1)C1=O)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1C(C=C1)=NC=C1N(CCOC1)C1=O)=O RIXFJPPIZZGLJO-UHFFFAOYSA-N 0.000 claims 1
- DYIBQFSHZSLOFM-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1C(C=C1)=NC=C1OC1COCC1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1C(C=C1)=NC=C1OC1COCC1)=O DYIBQFSHZSLOFM-UHFFFAOYSA-N 0.000 claims 1
- IYAKIGQGACFCBB-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1C1=NC=C(C(F)(F)F)C=C1)=O IYAKIGQGACFCBB-UHFFFAOYSA-N 0.000 claims 1
- CCPJAQPMLBCQJG-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1C1=NC=C(COC)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1C1=NC=C(COC)C=C1)=O CCPJAQPMLBCQJG-UHFFFAOYSA-N 0.000 claims 1
- VCDYMHGZYQEIHR-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1C1=NC=CC=C1)=O VCDYMHGZYQEIHR-UHFFFAOYSA-N 0.000 claims 1
- ONLXYNNYTAPICQ-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1C(C=C1)=NC=C1F)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1C(C=C1)=NC=C1F)=O ONLXYNNYTAPICQ-UHFFFAOYSA-N 0.000 claims 1
- BUTNLBYZDHBAAV-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1C(C=C1)=NC=C1N(CCOC1)C1=O)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1C(C=C1)=NC=C1N(CCOC1)C1=O)=O BUTNLBYZDHBAAV-UHFFFAOYSA-N 0.000 claims 1
- DVXIWUFNLAXYMU-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1C(C=C1)=NC=C1OCCOC)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1C(C=C1)=NC=C1OCCOC)=O DVXIWUFNLAXYMU-UHFFFAOYSA-N 0.000 claims 1
- AXGYMXIQCSUWFF-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1C1=NC=C(COC)C=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1C1=NC=C(COC)C=C1)=O AXGYMXIQCSUWFF-UHFFFAOYSA-N 0.000 claims 1
- COSYLMZYNGUKPD-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1C1=NC=CC=C1)=O COSYLMZYNGUKPD-UHFFFAOYSA-N 0.000 claims 1
- KWDLRKDSROFYPQ-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1N(CCOC1)C1=O)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1N(CCOC1)C1=O)=O KWDLRKDSROFYPQ-UHFFFAOYSA-N 0.000 claims 1
- SJMMSMXZYJKMND-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1OC1COCC1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C(C=C1)=NC=C1OC1COCC1)=O SJMMSMXZYJKMND-UHFFFAOYSA-N 0.000 claims 1
- LHYZFFVMWPRQEC-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C1=CC=CN=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C1=CC=CN=C1)=O LHYZFFVMWPRQEC-UHFFFAOYSA-N 0.000 claims 1
- SCCRSZWBXJAMBL-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C1=NC=CC(COC)=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C1=NC=CC(COC)=C1)=O SCCRSZWBXJAMBL-UHFFFAOYSA-N 0.000 claims 1
- SHFUHQSXZWFPTI-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(C)(=O)=O)=CC=C2)=C1C1=NC=CC=C1)=O SHFUHQSXZWFPTI-UHFFFAOYSA-N 0.000 claims 1
- XDGZELGUZGAHGB-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC(S(N)(=O)=O)=CC=C2)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC(S(N)(=O)=O)=CC=C2)=C1C1=NC=CC=C1)=O XDGZELGUZGAHGB-UHFFFAOYSA-N 0.000 claims 1
- BIZDCGARTHGZND-UHFFFAOYSA-N CC(NC(N=C1)=CC(NC2=NC=CC=C2S(C)(=O)=O)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(NC2=NC=CC=C2S(C)(=O)=O)=C1C1=NC=CC=C1)=O BIZDCGARTHGZND-UHFFFAOYSA-N 0.000 claims 1
- ASTDJXSVGWBLAV-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC(C=CC=C3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC(C=CC=C3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O ASTDJXSVGWBLAV-UHFFFAOYSA-N 0.000 claims 1
- ACXWXDLDTNFWDS-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC(C=CC=C3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC(C=CC=C3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1)=O ACXWXDLDTNFWDS-UHFFFAOYSA-N 0.000 claims 1
- IIKFFGCDILQOOU-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC(CN(C)CC3)=C3O2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC(CN(C)CC3)=C3O2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O IIKFFGCDILQOOU-UHFFFAOYSA-N 0.000 claims 1
- FBAXWUVOLOOFPT-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC(COCC3)=C3O2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC(COCC3)=C3O2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O FBAXWUVOLOOFPT-UHFFFAOYSA-N 0.000 claims 1
- CIEYPRROIQZFEP-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC(COCC3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC(COCC3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O CIEYPRROIQZFEP-UHFFFAOYSA-N 0.000 claims 1
- GPYSJUVPLPFOQW-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC=CC3=C2OCC2=C3N(C)N=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC=CC3=C2OCC2=C3N(C)N=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O GPYSJUVPLPFOQW-UHFFFAOYSA-N 0.000 claims 1
- VYSGFNGGTQAULL-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC=CC3=C2OCC2=C3N(C)N=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC=CC3=C2OCC2=C3N(C)N=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O VYSGFNGGTQAULL-UHFFFAOYSA-N 0.000 claims 1
- DRZXCMZNMJNOSX-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC=CC3=C2OCO3)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC=CC3=C2OCO3)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O DRZXCMZNMJNOSX-UHFFFAOYSA-N 0.000 claims 1
- WYIDSVARORZOMV-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC=CC3=C2OCO3)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC=CC3=C2OCO3)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O WYIDSVARORZOMV-UHFFFAOYSA-N 0.000 claims 1
- DGSGVPCRPKYGTN-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC=CO2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC=CO2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O DGSGVPCRPKYGTN-UHFFFAOYSA-N 0.000 claims 1
- XBDZHPUMYVRDTR-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC=CO2)C(NC2=NC(S(C)(=O)=O)=CC(C3(COCC3)OC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC=CO2)C(NC2=NC(S(C)(=O)=O)=CC(C3(COCC3)OC)=C2)=C1)=O XBDZHPUMYVRDTR-UHFFFAOYSA-N 0.000 claims 1
- NOJVOWZZSOIYRR-UHFFFAOYSA-N CC(NC1=NC=C(C2=CN(C)N=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CN(C)N=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O NOJVOWZZSOIYRR-UHFFFAOYSA-N 0.000 claims 1
- VIGRUMVGWLFVHC-UHFFFAOYSA-N CC(NC1=NC=C(C2=CN(C)N=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2OC)=C1)=O Chemical compound CC(NC1=NC=C(C2=CN(C)N=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2OC)=C1)=O VIGRUMVGWLFVHC-UHFFFAOYSA-N 0.000 claims 1
- WXZUGNDDAQTDLI-UHFFFAOYSA-N CC(NC1=NC=C(C2=CN(C)N=C2OC)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CN(C)N=C2OC)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O WXZUGNDDAQTDLI-UHFFFAOYSA-N 0.000 claims 1
- YPPYXXXMXMORRG-UHFFFAOYSA-N CC(NC1=NC=C(C2=CN(C)N=C2OC)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CN(C)N=C2OC)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O YPPYXXXMXMORRG-UHFFFAOYSA-N 0.000 claims 1
- QDWKJUYXQSOMDG-UHFFFAOYSA-N CC(NC1=NC=C(C2=CN(C=CC=N3)C3=N2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CN(C=CC=N3)C3=N2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O QDWKJUYXQSOMDG-UHFFFAOYSA-N 0.000 claims 1
- HLQGCELJCLJVIE-UHFFFAOYSA-N CC(NC1=NC=C(C2=CN(C=CC=N3)C3=N2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CN(C=CC=N3)C3=N2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O HLQGCELJCLJVIE-UHFFFAOYSA-N 0.000 claims 1
- OIEPHRBKITZCLV-UHFFFAOYSA-N CC(NC1=NC=C(C2=CNC=N2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CNC=N2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O OIEPHRBKITZCLV-UHFFFAOYSA-N 0.000 claims 1
- JAVUBGBJVIOAPR-UHFFFAOYSA-N CC(NC1=NC=C(C2=CNC=N2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CNC=N2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O JAVUBGBJVIOAPR-UHFFFAOYSA-N 0.000 claims 1
- ILMAHPPDPPOMMP-UHFFFAOYSA-N CC(NC1=NC=C(C2=NC(C=CC=C3)=C3N2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NC(C=CC=C3)=C3N2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O ILMAHPPDPPOMMP-UHFFFAOYSA-N 0.000 claims 1
- GYWYRZPIMLBDQS-UHFFFAOYSA-N CC(NC1=NC=C(C2=NC(C=CC=C3)=C3O2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NC(C=CC=C3)=C3O2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O GYWYRZPIMLBDQS-UHFFFAOYSA-N 0.000 claims 1
- BIGHKHVBOJUJKM-UHFFFAOYSA-N CC(NC1=NC=C(C2=NC(C=CC=C3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NC(C=CC=C3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O BIGHKHVBOJUJKM-UHFFFAOYSA-N 0.000 claims 1
- KHTMOVYUOLLUPK-UHFFFAOYSA-N CC(NC1=NC=C(C2=NC(CCN(C)C3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NC(CCN(C)C3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O KHTMOVYUOLLUPK-UHFFFAOYSA-N 0.000 claims 1
- TVJSQNBOSUNVEN-UHFFFAOYSA-N CC(NC1=NC=C(C2=NC(CCN(C)C3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(OCC3CC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NC(CCN(C)C3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(OCC3CC3)=C2)=C1)=O TVJSQNBOSUNVEN-UHFFFAOYSA-N 0.000 claims 1
- QGUXNUCEXYGKFT-UHFFFAOYSA-N CC(NC1=NC=C(C2=NC(CCOC3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NC(CCOC3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O QGUXNUCEXYGKFT-UHFFFAOYSA-N 0.000 claims 1
- JNKCPFROLVDGAH-UHFFFAOYSA-N CC(NC1=NC=C(C2=NC(CCOC3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NC(CCOC3)=C3S2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O JNKCPFROLVDGAH-UHFFFAOYSA-N 0.000 claims 1
- MQQXUTZYELTUKU-UHFFFAOYSA-N CC(NC1=NC=C(C2=NC=CN2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NC=CN2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O MQQXUTZYELTUKU-UHFFFAOYSA-N 0.000 claims 1
- HHEANJOOZSZDPR-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C(C)=C2)C(NC2=CC(OCCO)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C(C)=C2)C(NC2=CC(OCCO)=CC(S(C)(=O)=O)=C2)=C1)=O HHEANJOOZSZDPR-UHFFFAOYSA-N 0.000 claims 1
- LSJIMSSHUDFCOZ-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C(C)=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C(C)=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1)=O LSJIMSSHUDFCOZ-UHFFFAOYSA-N 0.000 claims 1
- ADNCTKBUJRSADN-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C(C)=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C(C)=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O ADNCTKBUJRSADN-UHFFFAOYSA-N 0.000 claims 1
- CNCPQXHWFCZCHO-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C(C)=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C(C)=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O CNCPQXHWFCZCHO-UHFFFAOYSA-N 0.000 claims 1
- VYQVSHJFODOIEK-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C(N3CCOCC3)=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C(N3CCOCC3)=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O VYQVSHJFODOIEK-UHFFFAOYSA-N 0.000 claims 1
- RLPZBMAIWRXWHW-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C(N3CCOCC3)=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C(N3CCOCC3)=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O RLPZBMAIWRXWHW-UHFFFAOYSA-N 0.000 claims 1
- RHYQTLCUXVJVOD-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC(C=C2)=NC(S(C)(=O)=O)=C2F)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC(C=C2)=NC(S(C)(=O)=O)=C2F)=C1)=O RHYQTLCUXVJVOD-UHFFFAOYSA-N 0.000 claims 1
- AXBLWYAVQXVUBX-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC(C=C2)=NC(S(C)(=O)=O)=C2OC)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC(C=C2)=NC(S(C)(=O)=O)=C2OC)=C1)=O AXBLWYAVQXVUBX-UHFFFAOYSA-N 0.000 claims 1
- ZVEROOBMFLNUAS-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC(N=C23)=CC=C2OCCCS3(=O)=O)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC(N=C23)=CC=C2OCCCS3(=O)=O)=C1)=O ZVEROOBMFLNUAS-UHFFFAOYSA-N 0.000 claims 1
- VQLZSLQXAHYRJP-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC(N=C23)=CC=C2OCCS3(=O)=O)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC(N=C23)=CC=C2OCCS3(=O)=O)=C1)=O VQLZSLQXAHYRJP-UHFFFAOYSA-N 0.000 claims 1
- RCOQEHCRVBZJMU-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(C#N)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(C#N)=CC(S(C)(=O)=O)=C2)=C1)=O RCOQEHCRVBZJMU-UHFFFAOYSA-N 0.000 claims 1
- YZIHXWQLJWTFBA-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(C(F)F)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(C(F)F)=CC(S(C)(=O)=O)=C2)=C1)=O YZIHXWQLJWTFBA-UHFFFAOYSA-N 0.000 claims 1
- VHGHZOYTEFTCHX-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(C)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(C)=CC(S(C)(=O)=O)=C2)=C1)=O VHGHZOYTEFTCHX-UHFFFAOYSA-N 0.000 claims 1
- FWIJAURIKVQFPC-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(COC)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(COC)=CC(S(C)(=O)=O)=C2)=C1)=O FWIJAURIKVQFPC-UHFFFAOYSA-N 0.000 claims 1
- YSVDSGYXCGQENR-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(Cl)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(Cl)=CC(S(C)(=O)=O)=C2)=C1)=O YSVDSGYXCGQENR-UHFFFAOYSA-N 0.000 claims 1
- IZVZPJANCQHHOA-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(F)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(F)=CC(S(C)(=O)=O)=C2)=C1)=O IZVZPJANCQHHOA-UHFFFAOYSA-N 0.000 claims 1
- SYUGCYAXSDFMDU-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OC(F)F)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OC(F)F)=CC(S(C)(=O)=O)=C2)=C1)=O SYUGCYAXSDFMDU-UHFFFAOYSA-N 0.000 claims 1
- SALLVICFANICHS-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OC)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OC)=CC(S(C)(=O)=O)=C2)=C1)=O SALLVICFANICHS-UHFFFAOYSA-N 0.000 claims 1
- GUGDZIUNVATWGP-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OC3CC3)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OC3CC3)=CC(S(C)(=O)=O)=C2)=C1)=O GUGDZIUNVATWGP-UHFFFAOYSA-N 0.000 claims 1
- SSLGREXHOJBCOW-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OCCC3)=C3C(S(C)(=O)=O)=N2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OCCC3)=C3C(S(C)(=O)=O)=N2)=C1)=O SSLGREXHOJBCOW-UHFFFAOYSA-N 0.000 claims 1
- WQFYUNIPSIGGAN-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OCCO)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OCCO)=CC(S(C)(=O)=O)=C2)=C1)=O WQFYUNIPSIGGAN-UHFFFAOYSA-N 0.000 claims 1
- CENCPLFHLWGBPR-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OCCOC)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(OCCOC)=CC(S(C)(=O)=O)=C2)=C1)=O CENCPLFHLWGBPR-UHFFFAOYSA-N 0.000 claims 1
- CCHHGRLOJCZUJG-JCNLHEQBSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(O[C@H](C3)C[C@@H]3O)=CC(S(C)(=O)=O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(O[C@H](C3)C[C@@H]3O)=CC(S(C)(=O)=O)=C2)=C1)=O CCHHGRLOJCZUJG-JCNLHEQBSA-N 0.000 claims 1
- WHOODUQSGVCBHL-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C2)=C1)=O WHOODUQSGVCBHL-UHFFFAOYSA-N 0.000 claims 1
- ZSIHBYDZDUYUHY-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(S(C)(=O)=O)=CC(OC(F)(F)F)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(S(C)(=O)=O)=CC(OC(F)(F)F)=C2)=C1)=O ZSIHBYDZDUYUHY-UHFFFAOYSA-N 0.000 claims 1
- JAGFHAUFQXIYFB-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC(S(C)(=O)=O)=CC=C2)=C1)=O JAGFHAUFQXIYFB-UHFFFAOYSA-N 0.000 claims 1
- MZKRFHAPVILNGP-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC=C(CCCS3(=O)=O)C3=N2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=CC=C(CCCS3(=O)=O)C3=N2)=C1)=O MZKRFHAPVILNGP-UHFFFAOYSA-N 0.000 claims 1
- VKLNZGIHIZESBC-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=C(C)C=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=C(C)C=C2)=C1)=O VKLNZGIHIZESBC-UHFFFAOYSA-N 0.000 claims 1
- IUUGACFCNGOKIU-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C#N)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C#N)=C2)=C1)=O IUUGACFCNGOKIU-UHFFFAOYSA-N 0.000 claims 1
- AFKFSFJWLLPLGO-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C(F)(F)F)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C(F)(F)F)=C2)=C1)=O AFKFSFJWLLPLGO-UHFFFAOYSA-N 0.000 claims 1
- RHKZSIRDNUJWAK-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C(F)F)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C(F)F)=C2)=C1)=O RHKZSIRDNUJWAK-UHFFFAOYSA-N 0.000 claims 1
- NRSCBEMFSVBLOY-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O NRSCBEMFSVBLOY-UHFFFAOYSA-N 0.000 claims 1
- SKNBNMXATIBEDA-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CC3)O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CC3)O)=C2)=C1)=O SKNBNMXATIBEDA-UHFFFAOYSA-N 0.000 claims 1
- FVZZETINHWSFAR-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O FVZZETINHWSFAR-UHFFFAOYSA-N 0.000 claims 1
- JDZSVIUGVBCQOS-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3(COCC3)O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3(COCC3)O)=C2)=C1)=O JDZSVIUGVBCQOS-UHFFFAOYSA-N 0.000 claims 1
- XMIOUXSSMWXSAQ-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3=CC=CC=C3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3=CC=CC=C3)=C2)=C1)=O XMIOUXSSMWXSAQ-UHFFFAOYSA-N 0.000 claims 1
- FQHUEHWTXQOOJN-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3=NN(C)C=C3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3=NN(C)C=C3)=C2)=C1)=O FQHUEHWTXQOOJN-UHFFFAOYSA-N 0.000 claims 1
- SBXOGTKOYBBZEC-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3CCOCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3CCOCC3)=C2)=C1)=O SBXOGTKOYBBZEC-UHFFFAOYSA-N 0.000 claims 1
- IEMLODBAWQQWPL-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3COCC3)=C2)=C1)=O IEMLODBAWQQWPL-UHFFFAOYSA-N 0.000 claims 1
- GAJNFURNBCSJJH-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(COC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(COC)=C2)=C1)=O GAJNFURNBCSJJH-UHFFFAOYSA-N 0.000 claims 1
- NBYGQHLYWYKSOC-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(Cl)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(Cl)=C2)=C1)=O NBYGQHLYWYKSOC-UHFFFAOYSA-N 0.000 claims 1
- PLUGMMZEZLURNP-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(N3CCOCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(N3CCOCC3)=C2)=C1)=O PLUGMMZEZLURNP-UHFFFAOYSA-N 0.000 claims 1
- OXUKZKCFMVEDAW-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC(C3)CC3OC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC(C3)CC3OC)=C2)=C1)=O OXUKZKCFMVEDAW-UHFFFAOYSA-N 0.000 claims 1
- INOQKNQNELDYEJ-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC(F)F)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC(F)F)=C2)=C1)=O INOQKNQNELDYEJ-UHFFFAOYSA-N 0.000 claims 1
- KPJLYNPVOIZWKU-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1)=O KPJLYNPVOIZWKU-UHFFFAOYSA-N 0.000 claims 1
- GFIMBEZZEHYNHW-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC3=CC=CC=C3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC3=CC=CC=C3)=C2)=C1)=O GFIMBEZZEHYNHW-UHFFFAOYSA-N 0.000 claims 1
- RILNAPCJBRGMLE-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC3CCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC3CCC3)=C2)=C1)=O RILNAPCJBRGMLE-UHFFFAOYSA-N 0.000 claims 1
- ZAPHUJUYDLVVDG-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC3CCCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC3CCCC3)=C2)=C1)=O ZAPHUJUYDLVVDG-UHFFFAOYSA-N 0.000 claims 1
- SVUNXYGOMKKLAX-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC3COC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC3COC3)=C2)=C1)=O SVUNXYGOMKKLAX-UHFFFAOYSA-N 0.000 claims 1
- WYFLTTVRHIAMAP-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC3COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC3COCC3)=C2)=C1)=O WYFLTTVRHIAMAP-UHFFFAOYSA-N 0.000 claims 1
- BSGRTCLGMZGLTD-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC#N)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC#N)=C2)=C1)=O BSGRTCLGMZGLTD-UHFFFAOYSA-N 0.000 claims 1
- LHUVUULVWWJHOB-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC(CO)O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC(CO)O)=C2)=C1)=O LHUVUULVWWJHOB-UHFFFAOYSA-N 0.000 claims 1
- QORZVAGZUJMSSE-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC3(CC3)O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC3(CC3)O)=C2)=C1)=O QORZVAGZUJMSSE-UHFFFAOYSA-N 0.000 claims 1
- HAAYHKWWTHWURU-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC3(CC3)OC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC3(CC3)OC)=C2)=C1)=O HAAYHKWWTHWURU-UHFFFAOYSA-N 0.000 claims 1
- HFAGYLFNTCGWMJ-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC3CC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC3CC3)=C2)=C1)=O HFAGYLFNTCGWMJ-UHFFFAOYSA-N 0.000 claims 1
- FUBKETYKTIYETG-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC3COC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCC3COC3)=C2)=C1)=O FUBKETYKTIYETG-UHFFFAOYSA-N 0.000 claims 1
- VPCHMCDFVZYPNW-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCO)=C2)=C1)=O VPCHMCDFVZYPNW-UHFFFAOYSA-N 0.000 claims 1
- ZXFNQURLUNMGAZ-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O ZXFNQURLUNMGAZ-UHFFFAOYSA-N 0.000 claims 1
- GBXBPKNIGKQACA-HDJSIYSDSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(O[C@H](C3)C[C@@H]3O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(O[C@H](C3)C[C@@H]3O)=C2)=C1)=O GBXBPKNIGKQACA-HDJSIYSDSA-N 0.000 claims 1
- GBXBPKNIGKQACA-OKILXGFUSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(O[C@H](C3)C[C@H]3O)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(O[C@H](C3)C[C@H]3O)=C2)=C1)=O GBXBPKNIGKQACA-OKILXGFUSA-N 0.000 claims 1
- CHRFTYJOTHYZJL-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC3=C2OCCO3)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC3=C2OCCO3)=C1)=O CHRFTYJOTHYZJL-UHFFFAOYSA-N 0.000 claims 1
- DOQPWZFWOQUDIB-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC3=C2OCO3)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC3=C2OCO3)=C1)=O DOQPWZFWOQUDIB-UHFFFAOYSA-N 0.000 claims 1
- HOTWHAHLEJNWLS-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O HOTWHAHLEJNWLS-UHFFFAOYSA-N 0.000 claims 1
- ABFGZUGOZFDMBF-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2C)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2C)=C1)=O ABFGZUGOZFDMBF-UHFFFAOYSA-N 0.000 claims 1
- IZBNYGQGIMDVLA-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2OC(F)F)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2OC(F)F)=C1)=O IZBNYGQGIMDVLA-UHFFFAOYSA-N 0.000 claims 1
- RVXGVLUXPWAZOA-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2OC)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2OC)=C1)=O RVXGVLUXPWAZOA-UHFFFAOYSA-N 0.000 claims 1
- KSWORERIZDECRU-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CN3C2=NC=C3)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C)(=O)=O)=CN3C2=NC=C3)=C1)=O KSWORERIZDECRU-UHFFFAOYSA-N 0.000 claims 1
- BBMCIHADMCSHPS-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C3CC3)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(C3CC3)(=O)=O)=CC=C2)=C1)=O BBMCIHADMCSHPS-UHFFFAOYSA-N 0.000 claims 1
- KSVXLFSOXRGPIF-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(N)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=C2)C(NC2=NC(S(N)(=O)=O)=CC=C2)=C1)=O KSVXLFSOXRGPIF-UHFFFAOYSA-N 0.000 claims 1
- IESPBIJTLNTVIZ-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C)C=N2)C(NC2=CC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C)C=N2)C(NC2=CC(S(C)(=O)=O)=CC=C2)=C1)=O IESPBIJTLNTVIZ-UHFFFAOYSA-N 0.000 claims 1
- AQKBBJWNACLEMH-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C3CC3)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C3CC3)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O AQKBBJWNACLEMH-UHFFFAOYSA-N 0.000 claims 1
- CCYALFYNNBNWFS-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C3CC3)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C3CC3)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O CCYALFYNNBNWFS-UHFFFAOYSA-N 0.000 claims 1
- GPZOTUHTWONUKN-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C3CC3)C=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C3CC3)C=C2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O GPZOTUHTWONUKN-UHFFFAOYSA-N 0.000 claims 1
- VOOYDQFNCRIBGZ-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C3COCC3)C=C2)C(NC2=CC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C3COCC3)C=C2)C(NC2=CC(S(C)(=O)=O)=CC=C2)=C1)=O VOOYDQFNCRIBGZ-UHFFFAOYSA-N 0.000 claims 1
- NJUXVUNDCVCZPE-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C3COCC3)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C3COCC3)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O NJUXVUNDCVCZPE-UHFFFAOYSA-N 0.000 claims 1
- CQOAKUDTUCNDFH-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C=CC=N3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C=CC=N3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O CQOAKUDTUCNDFH-UHFFFAOYSA-N 0.000 claims 1
- RZOWBVXCKGKGLO-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C=CC=N3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C=CC=N3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O RZOWBVXCKGKGLO-UHFFFAOYSA-N 0.000 claims 1
- MLICTBXBILFFGO-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C=CN=C3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C=CN=C3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O MLICTBXBILFFGO-UHFFFAOYSA-N 0.000 claims 1
- ACTPSSLGRVBZDU-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C=CN=C3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C=CN=C3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O ACTPSSLGRVBZDU-UHFFFAOYSA-N 0.000 claims 1
- KVTTZAVUGRJOQR-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C=NC=C3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C=NC=C3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O KVTTZAVUGRJOQR-UHFFFAOYSA-N 0.000 claims 1
- JGBPWXNAJMYZAR-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(C=NC=C3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(C=NC=C3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(OCCOC)=C2)=C1)=O JGBPWXNAJMYZAR-UHFFFAOYSA-N 0.000 claims 1
- KYILIDLQNIBZPS-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(CC(N3CCOCC3)=O)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(CC(N3CCOCC3)=O)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O KYILIDLQNIBZPS-UHFFFAOYSA-N 0.000 claims 1
- KFZATHGGQOQKHI-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(CCO3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(CCO3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O KFZATHGGQOQKHI-UHFFFAOYSA-N 0.000 claims 1
- DTNMLDOIYWMMGS-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(CCOC)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(CCOC)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O DTNMLDOIYWMMGS-UHFFFAOYSA-N 0.000 claims 1
- MGABYSQXYQZGPC-UHFFFAOYSA-N CC(NC1=NC=C(C2=NN(CCOC3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN(CCOC3)C3=C2)C(NC2=NC(S(C)(=O)=O)=CC(C)=C2)=C1)=O MGABYSQXYQZGPC-UHFFFAOYSA-N 0.000 claims 1
- PTKYHZNKISNLCW-MRXNPFEDSA-N CC(NC1=NC=C(C2=NN([C@H]3COCC3)C=C2)C(NC2=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN([C@H]3COCC3)C=C2)C(NC2=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C2)=C1)=O PTKYHZNKISNLCW-MRXNPFEDSA-N 0.000 claims 1
- KWWIJZIJBQKHAD-CQSZACIVSA-N CC(NC1=NC=C(C2=NN([C@H]3COCC3)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NN([C@H]3COCC3)C=C2)C(NC2=NC(S(C)(=O)=O)=CC(OC)=C2)=C1)=O KWWIJZIJBQKHAD-CQSZACIVSA-N 0.000 claims 1
- PQAHOPYDJVOICT-UHFFFAOYSA-N CC(NC1=NC=C(C2=NOC3=C2C=CC=C3)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NOC3=C2C=CC=C3)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O PQAHOPYDJVOICT-UHFFFAOYSA-N 0.000 claims 1
- CDHRJYHVBZJYKC-UHFFFAOYSA-N CC(NC1=NC=C(C2=NSC3=C2C=CC=C3)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=NSC3=C2C=CC=C3)C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C1)=O CDHRJYHVBZJYKC-UHFFFAOYSA-N 0.000 claims 1
- BPZALSPECPVNCO-UHFFFAOYSA-N CC1(C)N=C(C(C(NC2=NC(S(C)(=O)=O)=CC(C3CCOCC3)=C2)=C2)=CN=C2NC(C)=O)SC1 Chemical compound CC1(C)N=C(C(C(NC2=NC(S(C)(=O)=O)=CC(C3CCOCC3)=C2)=C2)=CN=C2NC(C)=O)SC1 BPZALSPECPVNCO-UHFFFAOYSA-N 0.000 claims 1
- IFMLATIVYURYKV-UHFFFAOYSA-N CC1(C)N=C(C(C(NC2=NC(S(C)(=O)=O)=CC=C2)=C2)=CN=C2NC(C)=O)SC1 Chemical compound CC1(C)N=C(C(C(NC2=NC(S(C)(=O)=O)=CC=C2)=C2)=CN=C2NC(C)=O)SC1 IFMLATIVYURYKV-UHFFFAOYSA-N 0.000 claims 1
- NZCYKXNFAHVECP-UHFFFAOYSA-N CC1(C)NC(C=CC(C(C(NC2=NC(S(C)(=O)=O)=CC(C3CCOCC3)=C2)=C2)=CN=C2NC(C)=O)=N2)=C2OC1 Chemical compound CC1(C)NC(C=CC(C(C(NC2=NC(S(C)(=O)=O)=CC(C3CCOCC3)=C2)=C2)=CN=C2NC(C)=O)=N2)=C2OC1 NZCYKXNFAHVECP-UHFFFAOYSA-N 0.000 claims 1
- NJYQUIANZHDDOF-UHFFFAOYSA-N CC1(C)OC2=CC(C(C(NC3=NC(S(C)(=O)=O)=CC(C4(CO)COCC4)=C3)=C3)=CN=C3NC(C)=O)=NN2C1 Chemical compound CC1(C)OC2=CC(C(C(NC3=NC(S(C)(=O)=O)=CC(C4(CO)COCC4)=C3)=C3)=CN=C3NC(C)=O)=NN2C1 NJYQUIANZHDDOF-UHFFFAOYSA-N 0.000 claims 1
- YUWHSMLHKFERSU-QGZVFWFLSA-N CC1(C)OC2=CC=C(C(C(NC(C=C3)=NC(S(C)(=O)=O)=C3N(CC3)C[C@@H]3OC)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC(C=C3)=NC(S(C)(=O)=O)=C3N(CC3)C[C@@H]3OC)=C3)=CN=C3NC(C)=O)N=C2OC1 YUWHSMLHKFERSU-QGZVFWFLSA-N 0.000 claims 1
- YUWHSMLHKFERSU-KRWDZBQOSA-N CC1(C)OC2=CC=C(C(C(NC(C=C3)=NC(S(C)(=O)=O)=C3N(CC3)C[C@H]3OC)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC(C=C3)=NC(S(C)(=O)=O)=C3N(CC3)C[C@H]3OC)=C3)=CN=C3NC(C)=O)N=C2OC1 YUWHSMLHKFERSU-KRWDZBQOSA-N 0.000 claims 1
- QTBYNZVPBMSRCA-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=C(C4CCOCC4)C=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=C(C4CCOCC4)C=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 QTBYNZVPBMSRCA-UHFFFAOYSA-N 0.000 claims 1
- DGFIFGAUQPSBEH-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 DGFIFGAUQPSBEH-UHFFFAOYSA-N 0.000 claims 1
- JKWWPVRFDKRWFO-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C(C=NC=C4)=C4C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C(C=NC=C4)=C4C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 JKWWPVRFDKRWFO-UHFFFAOYSA-N 0.000 claims 1
- QQGCIBLPVGDAOY-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C(C=NC=C4)=C4F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C(C=NC=C4)=C4F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 QQGCIBLPVGDAOY-UHFFFAOYSA-N 0.000 claims 1
- FYGNUPKWFLDHPJ-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C(C=NC=C4)=C4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C(C=NC=C4)=C4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 FYGNUPKWFLDHPJ-UHFFFAOYSA-N 0.000 claims 1
- YVYZOJVRNSYJHP-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C(F)(F)F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C(F)(F)F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 YVYZOJVRNSYJHP-UHFFFAOYSA-N 0.000 claims 1
- XOCMGTONKXMKDS-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 XOCMGTONKXMKDS-UHFFFAOYSA-N 0.000 claims 1
- UBJWHZXFPKIUJA-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4(CC4)C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4(CC4)C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 UBJWHZXFPKIUJA-UHFFFAOYSA-N 0.000 claims 1
- PPXGNBAJENVIEU-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4(CCOCC4)N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4(CCOCC4)N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 PPXGNBAJENVIEU-UHFFFAOYSA-N 0.000 claims 1
- UVWWMRQFDZAJCU-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4(CN)CCOCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4(CN)CCOCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 UVWWMRQFDZAJCU-UHFFFAOYSA-N 0.000 claims 1
- MRBJCYYLVXLHPZ-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=C(C)C=CN=C4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=C(C)C=CN=C4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 MRBJCYYLVXLHPZ-UHFFFAOYSA-N 0.000 claims 1
- YSBCCAILWQTHJV-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=C(C)ON=C4C)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=C(C)ON=C4C)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 YSBCCAILWQTHJV-UHFFFAOYSA-N 0.000 claims 1
- XMCYXPNSZKWRFC-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CC=C(C#N)N=C4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CC=C(C#N)N=C4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 XMCYXPNSZKWRFC-UHFFFAOYSA-N 0.000 claims 1
- VMGNTBPDEXWXDO-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CC=CN=C4C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CC=CN=C4C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 VMGNTBPDEXWXDO-UHFFFAOYSA-N 0.000 claims 1
- LAASNWGGJZJGQX-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CN=NC=C4C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CN=NC=C4C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 LAASNWGGJZJGQX-UHFFFAOYSA-N 0.000 claims 1
- NBIHLEZKDHFFSY-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CN=NC=C4C)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CN=NC=C4C)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 NBIHLEZKDHFFSY-UHFFFAOYSA-N 0.000 claims 1
- XUSGMBYRLLPYJL-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CN=NC=C4F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CN=NC=C4F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 XUSGMBYRLLPYJL-UHFFFAOYSA-N 0.000 claims 1
- ZVXXVOCEUCCUIY-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CN=NC=C4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CN=NC=C4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 ZVXXVOCEUCCUIY-UHFFFAOYSA-N 0.000 claims 1
- BKMWOUIUBZGHTD-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CSC=N4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=CSC=N4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 BKMWOUIUBZGHTD-UHFFFAOYSA-N 0.000 claims 1
- RTOLCWOBZSMQOT-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=NC=CC=C4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=NC=CC=C4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 RTOLCWOBZSMQOT-UHFFFAOYSA-N 0.000 claims 1
- HBJGOPMHBKPQBI-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=NC=CN=C4C)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4=NC=CN=C4C)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 HBJGOPMHBKPQBI-UHFFFAOYSA-N 0.000 claims 1
- KBGPHHXKGOOVMT-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4CCN(CC(F)(F)F)CC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4CCN(CC(F)(F)F)CC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 KBGPHHXKGOOVMT-UHFFFAOYSA-N 0.000 claims 1
- ZVOCDSJQCNDDMQ-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4CCOCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4CCOCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 ZVOCDSJQCNDDMQ-UHFFFAOYSA-N 0.000 claims 1
- BARMPFWYUATSRQ-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(CN(C(CS4)=O)C4=O)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(CN(C(CS4)=O)C4=O)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 BARMPFWYUATSRQ-UHFFFAOYSA-N 0.000 claims 1
- ACVHWOFYMLJNFM-OJCRERRGSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C(C4)C4C4)[C@@H]4C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C(C4)C4C4)[C@@H]4C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 ACVHWOFYMLJNFM-OJCRERRGSA-N 0.000 claims 1
- ACVHWOFYMLJNFM-ASNBIDDJSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C(C4)C4C4)[C@H]4C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C(C4)C4C4)[C@H]4C#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 ACVHWOFYMLJNFM-ASNBIDDJSA-N 0.000 claims 1
- PEFQUJRVRGVFAF-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C4)CC4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C4)CC4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 PEFQUJRVRGVFAF-UHFFFAOYSA-N 0.000 claims 1
- FKXPPXAQIFQFTR-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)CCC4(C)O)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)CCC4(C)O)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 FKXPPXAQIFQFTR-UHFFFAOYSA-N 0.000 claims 1
- ICMRJKUPQUGEJV-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)CCC4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)CCC4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 ICMRJKUPQUGEJV-UHFFFAOYSA-N 0.000 claims 1
- FGICTCOXMXXZPY-QGZVFWFLSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@@H]4OC(F)(F)F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@@H]4OC(F)(F)F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 FGICTCOXMXXZPY-QGZVFWFLSA-N 0.000 claims 1
- UGRKMLNEVXIRDM-GOSISDBHSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 UGRKMLNEVXIRDM-GOSISDBHSA-N 0.000 claims 1
- CTOLAHTYNXZSJV-LJQANCHMSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@@H]4OCCO)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@@H]4OCCO)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 CTOLAHTYNXZSJV-LJQANCHMSA-N 0.000 claims 1
- FGICTCOXMXXZPY-KRWDZBQOSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@H]4OC(F)(F)F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@H]4OC(F)(F)F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 FGICTCOXMXXZPY-KRWDZBQOSA-N 0.000 claims 1
- UGRKMLNEVXIRDM-SFHVURJKSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 UGRKMLNEVXIRDM-SFHVURJKSA-N 0.000 claims 1
- WCMYXSSVPLQDEI-IBGZPJMESA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@H]4OCC#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@H]4OCC#N)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 WCMYXSSVPLQDEI-IBGZPJMESA-N 0.000 claims 1
- CTOLAHTYNXZSJV-IBGZPJMESA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@H]4OCCO)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CC4)C[C@H]4OCCO)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 CTOLAHTYNXZSJV-IBGZPJMESA-N 0.000 claims 1
- WBILKVXNXREBME-IBGZPJMESA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CCC4)C[C@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(CCC4)C[C@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 WBILKVXNXREBME-IBGZPJMESA-N 0.000 claims 1
- CXDKKSDLVWCXKR-IERDGZPVSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C[C@H]4C#N)C[C@@H]4O)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C[C@H]4C#N)C[C@@H]4O)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 CXDKKSDLVWCXKR-IERDGZPVSA-N 0.000 claims 1
- HWRHBSDRPNYGJP-HXOBKFHXSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C[C@H]4C#N)C[C@@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C[C@H]4C#N)C[C@@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 HWRHBSDRPNYGJP-HXOBKFHXSA-N 0.000 claims 1
- CXDKKSDLVWCXKR-IIBYNOLFSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C[C@H]4C#N)C[C@H]4O)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C[C@H]4C#N)C[C@H]4O)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 CXDKKSDLVWCXKR-IIBYNOLFSA-N 0.000 claims 1
- HWRHBSDRPNYGJP-UZUQRXQVSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C[C@H]4C#N)C[C@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N(C[C@H]4C#N)C[C@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 HWRHBSDRPNYGJP-UZUQRXQVSA-N 0.000 claims 1
- PMKBHNFEXGGBAW-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4CC(C5)C5C4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4CC(C5)C5C4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 PMKBHNFEXGGBAW-UHFFFAOYSA-N 0.000 claims 1
- TZFCCCCQERXEFV-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4CC5(CC5)CC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4CC5(CC5)CC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 TZFCCCCQERXEFV-UHFFFAOYSA-N 0.000 claims 1
- SWSARXPMLGBLKX-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4CCCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4CCCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 SWSARXPMLGBLKX-UHFFFAOYSA-N 0.000 claims 1
- KSXDDSRHMHLOMB-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4CCOCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4CCOCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 KSXDDSRHMHLOMB-UHFFFAOYSA-N 0.000 claims 1
- PEQVYEVVTVFJRA-SFHVURJKSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4C[C@@H](COC)CC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4C[C@@H](COC)CC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 PEQVYEVVTVFJRA-SFHVURJKSA-N 0.000 claims 1
- PEQVYEVVTVFJRA-GOSISDBHSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4C[C@H](COC)CC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4C[C@H](COC)CC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 PEQVYEVVTVFJRA-GOSISDBHSA-N 0.000 claims 1
- SWAOOXFHKPGJCD-GOSISDBHSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4[C@@H](COC)CCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4[C@@H](COC)CCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 SWAOOXFHKPGJCD-GOSISDBHSA-N 0.000 claims 1
- SWAOOXFHKPGJCD-SFHVURJKSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4[C@H](COC)CCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(N4[C@H](COC)CCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 SWAOOXFHKPGJCD-SFHVURJKSA-N 0.000 claims 1
- AJYXMCXQFAWQEN-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(OC(F)F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(OC(F)F)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 AJYXMCXQFAWQEN-UHFFFAOYSA-N 0.000 claims 1
- BRDKHBSREKWDRJ-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 BRDKHBSREKWDRJ-UHFFFAOYSA-N 0.000 claims 1
- XVGLOEVSHUACDT-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(OC)=C3OC)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(OC)=C3OC)=C3)=CN=C3NC(C)=O)N=C2OC1 XVGLOEVSHUACDT-UHFFFAOYSA-N 0.000 claims 1
- AWFFBUVJPUDCEO-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(OC4CCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(OC4CCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 AWFFBUVJPUDCEO-UHFFFAOYSA-N 0.000 claims 1
- ARIBCGBFBKBELM-IYARVYRRSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(O[C@H](CC4)CC[C@@H]4O)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(O[C@H](CC4)CC[C@@H]4O)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 ARIBCGBFBKBELM-IYARVYRRSA-N 0.000 claims 1
- OXSNCBQOAQDTCM-WGSAOQKQSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(O[C@H](CC4)CC[C@@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(O[C@H](CC4)CC[C@@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 OXSNCBQOAQDTCM-WGSAOQKQSA-N 0.000 claims 1
- OXSNCBQOAQDTCM-KDURUIRLSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(O[C@H](CC4)CC[C@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(O[C@H](CC4)CC[C@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 OXSNCBQOAQDTCM-KDURUIRLSA-N 0.000 claims 1
- JGELQOCOYHTDSY-MRXNPFEDSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@@H](C4)C4(Cl)Cl)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@@H](C4)C4(Cl)Cl)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 JGELQOCOYHTDSY-MRXNPFEDSA-N 0.000 claims 1
- BMDNYZPBLJRRLZ-INIZCTEOSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@@H]4COCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@@H]4COCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 BMDNYZPBLJRRLZ-INIZCTEOSA-N 0.000 claims 1
- KLIWMZXVUDSRTG-KRWDZBQOSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@@H]4COCCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@@H]4COCCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 KLIWMZXVUDSRTG-KRWDZBQOSA-N 0.000 claims 1
- JGELQOCOYHTDSY-INIZCTEOSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@H](C4)C4(Cl)Cl)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@H](C4)C4(Cl)Cl)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 JGELQOCOYHTDSY-INIZCTEOSA-N 0.000 claims 1
- RWWKJGKRTMZJSG-SAABIXHNSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@H](C4)C[C@@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@H](C4)C[C@@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 RWWKJGKRTMZJSG-SAABIXHNSA-N 0.000 claims 1
- RWWKJGKRTMZJSG-MAEOIBBWSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@H](C4)C[C@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@H](C4)C[C@H]4OC)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 RWWKJGKRTMZJSG-MAEOIBBWSA-N 0.000 claims 1
- BMDNYZPBLJRRLZ-MRXNPFEDSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@H]4COCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@H]4COCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 BMDNYZPBLJRRLZ-MRXNPFEDSA-N 0.000 claims 1
- KLIWMZXVUDSRTG-QGZVFWFLSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@H]4COCCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC([C@H]4COCCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 KLIWMZXVUDSRTG-QGZVFWFLSA-N 0.000 claims 1
- JUXYPRLBOYVRID-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC4=C3OCCO4)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC4=C3OCCO4)=C3)=CN=C3NC(C)=O)N=C2OC1 JUXYPRLBOYVRID-UHFFFAOYSA-N 0.000 claims 1
- SPWURQZSKGWTEF-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC4=C3OCO4)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC4=C3OCO4)=C3)=CN=C3NC(C)=O)N=C2OC1 SPWURQZSKGWTEF-UHFFFAOYSA-N 0.000 claims 1
- JMTBTHGOQUVGOV-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC=C3C3CCOCC3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC=C3C3CCOCC3)=C3)=CN=C3NC(C)=O)N=C2OC1 JMTBTHGOQUVGOV-UHFFFAOYSA-N 0.000 claims 1
- JZUPYSLUFSJIGO-QGZVFWFLSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC=C3N(CC3)C[C@@H]3OC)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC=C3N(CC3)C[C@@H]3OC)=C3)=CN=C3NC(C)=O)N=C2OC1 JZUPYSLUFSJIGO-QGZVFWFLSA-N 0.000 claims 1
- JZUPYSLUFSJIGO-KRWDZBQOSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC=C3N(CC3)C[C@H]3OC)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC=C3N(CC3)C[C@H]3OC)=C3)=CN=C3NC(C)=O)N=C2OC1 JZUPYSLUFSJIGO-KRWDZBQOSA-N 0.000 claims 1
- YREJMXXFOLNLAW-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CN(C)C3=O)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CN(C)C3=O)=C3)=CN=C3NC(C)=O)N=C2OC1 YREJMXXFOLNLAW-UHFFFAOYSA-N 0.000 claims 1
- OORMTKPXPUXTCQ-UHFFFAOYSA-N CC1(C)OC2=CC=C(C(N=NC(NC(C)=O)=C3)=C3NC3=NC(S(C)(=O)=O)=CC(C4CCOCC4)=C3)N=C2OC1 Chemical compound CC1(C)OC2=CC=C(C(N=NC(NC(C)=O)=C3)=C3NC3=NC(S(C)(=O)=O)=CC(C4CCOCC4)=C3)N=C2OC1 OORMTKPXPUXTCQ-UHFFFAOYSA-N 0.000 claims 1
- PIFULJPLTFLTQJ-UHFFFAOYSA-N CC1(C)OC2=NC(C(C(NC(C=C3C)=NC(S(C)(=O)=O)=C3F)=C3)=CN=C3NC(C)=O)=CC=C2OC1 Chemical compound CC1(C)OC2=NC(C(C(NC(C=C3C)=NC(S(C)(=O)=O)=C3F)=C3)=CN=C3NC(C)=O)=CC=C2OC1 PIFULJPLTFLTQJ-UHFFFAOYSA-N 0.000 claims 1
- SXRLYFCAQHEAHL-UHFFFAOYSA-N CC1(C)OC2=NC(C(C(NC3=NC(S(C)(=O)=O)=CC(C4CCOCC4)=C3)=C3)=CN=C3NC(C)=O)=CC=C2OC1 Chemical compound CC1(C)OC2=NC(C(C(NC3=NC(S(C)(=O)=O)=CC(C4CCOCC4)=C3)=C3)=CN=C3NC(C)=O)=CC=C2OC1 SXRLYFCAQHEAHL-UHFFFAOYSA-N 0.000 claims 1
- MBMOCNIDVPOGBI-UHFFFAOYSA-N CC1(C)OC2=NC(C(C(NC3=NC(S(C)(=O)=O)=CC(N4CCOCC4)=C3)=C3)=CN=C3NC(C)=O)=CC=C2OC1 Chemical compound CC1(C)OC2=NC(C(C(NC3=NC(S(C)(=O)=O)=CC(N4CCOCC4)=C3)=C3)=CN=C3NC(C)=O)=CC=C2OC1 MBMOCNIDVPOGBI-UHFFFAOYSA-N 0.000 claims 1
- ABJRGQFLFPDONJ-UHFFFAOYSA-N CC1(C)OC2=NC(C(C(NC3=NC(S(C)(=O)=O)=CC(OC)=C3)=C3)=CN=C3NC(C)=O)=CC=C2OC1 Chemical compound CC1(C)OC2=NC(C(C(NC3=NC(S(C)(=O)=O)=CC(OC)=C3)=C3)=CN=C3NC(C)=O)=CC=C2OC1 ABJRGQFLFPDONJ-UHFFFAOYSA-N 0.000 claims 1
- ZKEXBJVHQHTJJJ-UHFFFAOYSA-N CC1(C)OC2=NC(C(C(NC3=NC(S(C)(=O)=O)=CC(OCC4OCCOC4)=C3)=C3)=CN=C3NC(C)=O)=CC=C2OC1 Chemical compound CC1(C)OC2=NC(C(C(NC3=NC(S(C)(=O)=O)=CC(OCC4OCCOC4)=C3)=C3)=CN=C3NC(C)=O)=CC=C2OC1 ZKEXBJVHQHTJJJ-UHFFFAOYSA-N 0.000 claims 1
- FZMIOXBWKPQIKF-UHFFFAOYSA-N CC1(C)OC2=NC(C(C(NC3=NC(S(C)(=O)=O)=CN=C3)=C3)=CN=C3NC(C)=O)=CC=C2OC1 Chemical compound CC1(C)OC2=NC(C(C(NC3=NC(S(C)(=O)=O)=CN=C3)=C3)=CN=C3NC(C)=O)=CC=C2OC1 FZMIOXBWKPQIKF-UHFFFAOYSA-N 0.000 claims 1
- UWBWDINMGWIJNU-UHFFFAOYSA-N CC1(COC2=CC(NC3=CC(NC(C)=O)=NC=C3C3=CC=C4OC(C)(C)COC4=N3)=NC(S(C)(=O)=O)=C2)COC1 Chemical compound CC1(COC2=CC(NC3=CC(NC(C)=O)=NC=C3C3=CC=C4OC(C)(C)COC4=N3)=NC(S(C)(=O)=O)=C2)COC1 UWBWDINMGWIJNU-UHFFFAOYSA-N 0.000 claims 1
- UGHVXSCEKIWSBJ-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=CC(C#N)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=CC(C#N)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O UGHVXSCEKIWSBJ-UHFFFAOYSA-N 0.000 claims 1
- NFCUUJVUSAVDFX-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=CC(C)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=CC(C)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O NFCUUJVUSAVDFX-UHFFFAOYSA-N 0.000 claims 1
- CCPVVKFJBNQGMZ-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=CC(COC)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=CC(COC)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O CCPVVKFJBNQGMZ-UHFFFAOYSA-N 0.000 claims 1
- UKMUNNVALLFAEB-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=CC(OC)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=CC(OC)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O UKMUNNVALLFAEB-UHFFFAOYSA-N 0.000 claims 1
- XIUFXPDIERMQAS-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=CC(OCC2CC2)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=CC(OCC2CC2)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O XIUFXPDIERMQAS-UHFFFAOYSA-N 0.000 claims 1
- FBSFWYINQHEKLO-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=CC(OCCO)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=CC(OCCO)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O FBSFWYINQHEKLO-UHFFFAOYSA-N 0.000 claims 1
- AMPKVCXGZBIUQG-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=CC(OCCOC)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=CC(OCCOC)=CC(S(C)(=O)=O)=C1)=C1)=CN=C1NC(C)=O AMPKVCXGZBIUQG-UHFFFAOYSA-N 0.000 claims 1
- ADYKKVKCCBKXBI-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=CC(S(C)(=O)=O)=CC(C(F)(F)F)=C1)=C1)=CN=C1NC(C)=O ADYKKVKCCBKXBI-UHFFFAOYSA-N 0.000 claims 1
- WCAIVFLOVNLQMG-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=CC(S(C)(=O)=O)=CC=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=CC(S(C)(=O)=O)=CC=C1)=C1)=CN=C1NC(C)=O WCAIVFLOVNLQMG-UHFFFAOYSA-N 0.000 claims 1
- VFELDAWKPFGHCJ-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(COC)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(COC)=C1)=C1)=CN=C1NC(C)=O VFELDAWKPFGHCJ-UHFFFAOYSA-N 0.000 claims 1
- IBPJGQGYRZUAIH-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OC(C)C)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OC(C)C)=C1)=C1)=CN=C1NC(C)=O IBPJGQGYRZUAIH-UHFFFAOYSA-N 0.000 claims 1
- DSRFBUFOTLOCQW-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OC2CCCC2)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OC2CCCC2)=C1)=C1)=CN=C1NC(C)=O DSRFBUFOTLOCQW-UHFFFAOYSA-N 0.000 claims 1
- QWSHNPRKZCFIIU-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OCC)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OCC)=C1)=C1)=CN=C1NC(C)=O QWSHNPRKZCFIIU-UHFFFAOYSA-N 0.000 claims 1
- ZYKKIOGSBVQPSN-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OCCO)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OCCO)=C1)=C1)=CN=C1NC(C)=O ZYKKIOGSBVQPSN-UHFFFAOYSA-N 0.000 claims 1
- DACQQLBLUOWLRJ-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OCCOC)=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC(OCCOC)=C1)=C1)=CN=C1NC(C)=O DACQQLBLUOWLRJ-UHFFFAOYSA-N 0.000 claims 1
- WOQPTMNCMRJSIG-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC=C1)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC=C1)=C1)=CN=C1NC(C)=O WOQPTMNCMRJSIG-UHFFFAOYSA-N 0.000 claims 1
- OTZRWHGFNBRFIF-UHFFFAOYSA-N CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC=C1OC(C)C)=C1)=CN=C1NC(C)=O Chemical compound CCN(C=C1)N=C1C(C(NC1=NC(S(C)(=O)=O)=CC=C1OC(C)C)=C1)=CN=C1NC(C)=O OTZRWHGFNBRFIF-UHFFFAOYSA-N 0.000 claims 1
- KQFKVOXJUKVPGU-UHFFFAOYSA-N CCOC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2F)=NC(S(C)(=O)=O)=C1 Chemical compound CCOC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2F)=NC(S(C)(=O)=O)=C1 KQFKVOXJUKVPGU-UHFFFAOYSA-N 0.000 claims 1
- NULRYUNMNLCKST-CALCHBBNSA-N CCOC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1 Chemical compound CCOC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1 NULRYUNMNLCKST-CALCHBBNSA-N 0.000 claims 1
- HPYHEMLOZLVGRH-UHFFFAOYSA-N CCOC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2OCCOC)=NC(S(C)(=O)=O)=C1 Chemical compound CCOC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2OCCOC)=NC(S(C)(=O)=O)=C1 HPYHEMLOZLVGRH-UHFFFAOYSA-N 0.000 claims 1
- JHVAYFVOGMSWCE-UHFFFAOYSA-N CCOC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CCOC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1 JHVAYFVOGMSWCE-UHFFFAOYSA-N 0.000 claims 1
- JBCQMVZMOQFVTQ-UHFFFAOYSA-N CCOC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(F)(F)F)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CCOC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(F)(F)F)C=C2)=NC(S(C)(=O)=O)=C1 JBCQMVZMOQFVTQ-UHFFFAOYSA-N 0.000 claims 1
- PAMWOKUFXATUFV-UHFFFAOYSA-N CCOC1=CC(NC2=CC(NC(C)=O)=NC=C2C(N=C2)=CC3=C2OCCO3)=NC(S(C)(=O)=O)=C1 Chemical compound CCOC1=CC(NC2=CC(NC(C)=O)=NC=C2C(N=C2)=CC3=C2OCCO3)=NC(S(C)(=O)=O)=C1 PAMWOKUFXATUFV-UHFFFAOYSA-N 0.000 claims 1
- VAKKANSZPUKKLO-UHFFFAOYSA-N CCOC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCOC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound CCOC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCOC3=N2)=NC(S(C)(=O)=O)=C1 VAKKANSZPUKKLO-UHFFFAOYSA-N 0.000 claims 1
- FPDKGFWWHPZSQK-UHFFFAOYSA-N CCOC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C(C)=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CCOC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C(C)=C2)=NC(S(C)(=O)=O)=C1 FPDKGFWWHPZSQK-UHFFFAOYSA-N 0.000 claims 1
- XMGBYIAEJYBDJX-UHFFFAOYSA-N CCOC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CCOC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1 XMGBYIAEJYBDJX-UHFFFAOYSA-N 0.000 claims 1
- TWXWPQJWUGUEBU-FQEVSTJZSA-N CCO[C@@H](CCC1)CN1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound CCO[C@@H](CCC1)CN1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 TWXWPQJWUGUEBU-FQEVSTJZSA-N 0.000 claims 1
- TWXWPQJWUGUEBU-HXUWFJFHSA-N CCO[C@H](CCC1)CN1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound CCO[C@H](CCC1)CN1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 TWXWPQJWUGUEBU-HXUWFJFHSA-N 0.000 claims 1
- YZMZIXOWADMCGW-UHFFFAOYSA-N CCS(C1=CC(OC(C)C)=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=N1)(=O)=O Chemical compound CCS(C1=CC(OC(C)C)=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=N1)(=O)=O YZMZIXOWADMCGW-UHFFFAOYSA-N 0.000 claims 1
- YZCILORIBIJWTR-UHFFFAOYSA-N CCS(C1=CC(OC(C)C)=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=N1)(=O)=O Chemical compound CCS(C1=CC(OC(C)C)=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=N1)(=O)=O YZCILORIBIJWTR-UHFFFAOYSA-N 0.000 claims 1
- FPAUKKHQJOZVBO-UHFFFAOYSA-N CCS(C1=CC=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=N1)(=O)=O Chemical compound CCS(C1=CC=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=N1)(=O)=O FPAUKKHQJOZVBO-UHFFFAOYSA-N 0.000 claims 1
- QJJQMTMESGNQJM-QRVBRYPASA-N CC[C@@H](C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC[C@@H](C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1 QJJQMTMESGNQJM-QRVBRYPASA-N 0.000 claims 1
- ABJLNMAKVURGGE-OAHLLOKOSA-N CC[C@@H](C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC[C@@H](C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1 ABJLNMAKVURGGE-OAHLLOKOSA-N 0.000 claims 1
- FTGLBRZHHLOXHE-CYBMUJFWSA-N CC[C@@H](C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC[C@@H](C)OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1 FTGLBRZHHLOXHE-CYBMUJFWSA-N 0.000 claims 1
- ABJLNMAKVURGGE-HNNXBMFYSA-N CC[C@H](C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1 Chemical compound CC[C@H](C)OC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1 ABJLNMAKVURGGE-HNNXBMFYSA-N 0.000 claims 1
- VMBYONNJQNQQNG-UHFFFAOYSA-N CS(C1=CC=CC(NC(C=C(NC(C2CC2)=O)N=C2)=C2C2=NC=CC=C2)=C1)(=O)=O Chemical compound CS(C1=CC=CC(NC(C=C(NC(C2CC2)=O)N=C2)=C2C2=NC=CC=C2)=C1)(=O)=O VMBYONNJQNQQNG-UHFFFAOYSA-N 0.000 claims 1
- XKVITUMJUHNQHP-IRXDYDNUSA-N C[C@@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1 Chemical compound C[C@@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(C)=C1 XKVITUMJUHNQHP-IRXDYDNUSA-N 0.000 claims 1
- CIFKTVWJTBSKJG-AWEZNQCLSA-N C[C@@H](C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCC(C)(C)OC3=N2)=NC(S(C)(=O)=O)=C1)OC Chemical compound C[C@@H](C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCC(C)(C)OC3=N2)=NC(S(C)(=O)=O)=C1)OC CIFKTVWJTBSKJG-AWEZNQCLSA-N 0.000 claims 1
- PPXSXDOVWRWUBW-INIZCTEOSA-N C[C@@H](CC1)CN1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound C[C@@H](CC1)CN1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 PPXSXDOVWRWUBW-INIZCTEOSA-N 0.000 claims 1
- LXHJFWOVJLAPPL-LBPRGKRZSA-N C[C@@H](COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(F)(F)F)C=C2)=NC(S(C)(=O)=O)=C1)O Chemical compound C[C@@H](COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(F)(F)F)C=C2)=NC(S(C)(=O)=O)=C1)O LXHJFWOVJLAPPL-LBPRGKRZSA-N 0.000 claims 1
- KKSAFMNZSUOVEG-ZDUSSCGKSA-N C[C@@H](COC1=CC(S(C)(=O)=O)=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=C1)O Chemical compound C[C@@H](COC1=CC(S(C)(=O)=O)=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=C1)O KKSAFMNZSUOVEG-ZDUSSCGKSA-N 0.000 claims 1
- RBDXCCXERUCFDM-INIZCTEOSA-N C[C@@H](COCC1)N1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound C[C@@H](COCC1)N1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 RBDXCCXERUCFDM-INIZCTEOSA-N 0.000 claims 1
- ILNVQTNBWXNDMI-INIZCTEOSA-N C[C@@H](COCC1)N1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCC(C)(C)OC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound C[C@@H](COCC1)N1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCC(C)(C)OC3=N2)=NC(S(C)(=O)=O)=C1 ILNVQTNBWXNDMI-INIZCTEOSA-N 0.000 claims 1
- CCNIRRFGTLELRH-CALCHBBNSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(C#N)=CC(S(C)(=O)=O)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(C#N)=CC(S(C)(=O)=O)=C1 CCNIRRFGTLELRH-CALCHBBNSA-N 0.000 claims 1
- NISDZLDVKLWKBQ-IYBDPMFKSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(F)=CC(S(C)(=O)=O)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(F)=CC(S(C)(=O)=O)=C1 NISDZLDVKLWKBQ-IYBDPMFKSA-N 0.000 claims 1
- XGEUTLKIVDLSPN-CALCHBBNSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OC)=CC(S(C)(=O)=O)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OC)=CC(S(C)(=O)=O)=C1 XGEUTLKIVDLSPN-CALCHBBNSA-N 0.000 claims 1
- YZAIEBNRORYEES-KDURUIRLSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OCC2CC2)=CC(S(C)(=O)=O)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(OCC2CC2)=CC(S(C)(=O)=O)=C1 YZAIEBNRORYEES-KDURUIRLSA-N 0.000 claims 1
- IZNANRPTMAKMBN-CALCHBBNSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(S(C)(=O)=O)=CC=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=CC(S(C)(=O)=O)=CC=C1 IZNANRPTMAKMBN-CALCHBBNSA-N 0.000 claims 1
- QAIYADTUTPHRTL-HDICACEKSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(N(C2)CC2OC)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(N(C2)CC2OC)=C1 QAIYADTUTPHRTL-HDICACEKSA-N 0.000 claims 1
- WLXDUWAQURWGRB-HDICACEKSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2CC2)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCC2CC2)=C1 WLXDUWAQURWGRB-HDICACEKSA-N 0.000 claims 1
- ZAAQCUFCSRGSCF-HDICACEKSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCCOC)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC(OCCOC)=C1 ZAAQCUFCSRGSCF-HDICACEKSA-N 0.000 claims 1
- BDGNLNFIPZWORX-IYBDPMFKSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC2=C1OCCO2 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC2=C1OCCO2 BDGNLNFIPZWORX-IYBDPMFKSA-N 0.000 claims 1
- BTZANEXZJQUCJQ-IYBDPMFKSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1NC1=NC(S(C)(=O)=O)=CC=C1 BTZANEXZJQUCJQ-IYBDPMFKSA-N 0.000 claims 1
- DBUCYUMATVXWIU-GASCZTMLSA-N C[C@H](C1)O[C@@H](C)CN1C1=CC(NC2=CC(NC(C)=O)=NC=C2C(N=N2)=CC=C2OC)=NC(S(C)(=O)=O)=C1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C1=CC(NC2=CC(NC(C)=O)=NC=C2C(N=N2)=CC=C2OC)=NC(S(C)(=O)=O)=C1 DBUCYUMATVXWIU-GASCZTMLSA-N 0.000 claims 1
- WJBKRRAWFVPDLB-GLLFSFACSA-N C[C@H](C1)O[C@@H](C)CN1C1=CC=C(C(C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C2)=CN=C2NC(C)=O)N=N1 Chemical compound C[C@H](C1)O[C@@H](C)CN1C1=CC=C(C(C(NC2=NC(S(C)(=O)=O)=CC(C3(CO)COCC3)=C2)=C2)=CN=C2NC(C)=O)N=N1 WJBKRRAWFVPDLB-GLLFSFACSA-N 0.000 claims 1
- CIFKTVWJTBSKJG-CQSZACIVSA-N C[C@H](C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCC(C)(C)OC3=N2)=NC(S(C)(=O)=O)=C1)OC Chemical compound C[C@H](C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCC(C)(C)OC3=N2)=NC(S(C)(=O)=O)=C1)OC CIFKTVWJTBSKJG-CQSZACIVSA-N 0.000 claims 1
- WMKUPFDOKJURML-KURKYZTESA-N C[C@H](COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1)O Chemical compound C[C@H](COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2N2C[C@H](C)O[C@H](C)C2)=NC(S(C)(=O)=O)=C1)O WMKUPFDOKJURML-KURKYZTESA-N 0.000 claims 1
- RVECHBSGNPMCSN-MRXNPFEDSA-N C[C@H](COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2OCCOC)=NC(S(C)(=O)=O)=C1)OC Chemical compound C[C@H](COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C(C=C2)=NC=C2OCCOC)=NC(S(C)(=O)=O)=C1)OC RVECHBSGNPMCSN-MRXNPFEDSA-N 0.000 claims 1
- STKIHWLOFWZPOS-CQSZACIVSA-N C[C@H](COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1)O Chemical compound C[C@H](COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(C(C)(C)O)C=C2)=NC(S(C)(=O)=O)=C1)O STKIHWLOFWZPOS-CQSZACIVSA-N 0.000 claims 1
- XGGOHJVRABBIRE-OAHLLOKOSA-N C[C@H](COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(COC)C=C2)=NC(S(C)(=O)=O)=C1)OC Chemical compound C[C@H](COC1=CC(NC(C=C(NC(C)=O)N=C2)=C2C2=NC=C(COC)C=C2)=NC(S(C)(=O)=O)=C1)OC XGGOHJVRABBIRE-OAHLLOKOSA-N 0.000 claims 1
- XEKJWGQFEFJYHQ-CQSZACIVSA-N C[C@H](COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C(C)=C2)=NC(S(C)(=O)=O)=C1)OC Chemical compound C[C@H](COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C(C)=C2)=NC(S(C)(=O)=O)=C1)OC XEKJWGQFEFJYHQ-CQSZACIVSA-N 0.000 claims 1
- YCPIUTSURRDLIE-GFCCVEGCSA-N C[C@H](COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)O Chemical compound C[C@H](COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)O YCPIUTSURRDLIE-GFCCVEGCSA-N 0.000 claims 1
- RNTVRCXLFIJIPL-CYBMUJFWSA-N C[C@H](COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)OC Chemical compound C[C@H](COC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=NC(S(C)(=O)=O)=C1)OC RNTVRCXLFIJIPL-CYBMUJFWSA-N 0.000 claims 1
- KKSAFMNZSUOVEG-CYBMUJFWSA-N C[C@H](COC1=CC(S(C)(=O)=O)=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=C1)O Chemical compound C[C@H](COC1=CC(S(C)(=O)=O)=CC(NC2=CC(NC(C)=O)=NC=C2C2=NN(C)C=C2)=C1)O KKSAFMNZSUOVEG-CYBMUJFWSA-N 0.000 claims 1
- RBDXCCXERUCFDM-MRXNPFEDSA-N C[C@H](COCC1)N1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound C[C@H](COCC1)N1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 RBDXCCXERUCFDM-MRXNPFEDSA-N 0.000 claims 1
- ILNVQTNBWXNDMI-MRXNPFEDSA-N C[C@H](COCC1)N1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCC(C)(C)OC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound C[C@H](COCC1)N1C1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCC(C)(C)OC3=N2)=NC(S(C)(=O)=O)=C1 ILNVQTNBWXNDMI-MRXNPFEDSA-N 0.000 claims 1
- ZVOCDSJQCNDDMQ-XERRXZQWSA-N [2H]C([2H])([2H])C1(C([2H])([2H])[2H])OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4CCOCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound [2H]C([2H])([2H])C1(C([2H])([2H])[2H])OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(C4CCOCC4)=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 ZVOCDSJQCNDDMQ-XERRXZQWSA-N 0.000 claims 1
- BRDKHBSREKWDRJ-WVZRYRIDSA-N [2H]C([2H])([2H])C1(C([2H])([2H])[2H])OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(OC([2H])([2H])[2H])=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 Chemical compound [2H]C([2H])([2H])C1(C([2H])([2H])[2H])OC2=CC=C(C(C(NC3=NC(S(C)(=O)=O)=CC(OC([2H])([2H])[2H])=C3)=C3)=CN=C3NC(C)=O)N=C2OC1 BRDKHBSREKWDRJ-WVZRYRIDSA-N 0.000 claims 1
- MKAPVMYGHAFGBU-GKOSEXJESA-N [2H]C([2H])([2H])OC1=CC(NC2=CC(NC(C)=O)=NC=C2C(N=N2)=CC=C2OC(C)C)=NC(S(C)(=O)=O)=C1 Chemical compound [2H]C([2H])([2H])OC1=CC(NC2=CC(NC(C)=O)=NC=C2C(N=N2)=CC=C2OC(C)C)=NC(S(C)(=O)=O)=C1 MKAPVMYGHAFGBU-GKOSEXJESA-N 0.000 claims 1
- BRDKHBSREKWDRJ-GKOSEXJESA-N [2H]C([2H])([2H])OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound [2H]C([2H])([2H])OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OC(C)(C)COC3=N2)=NC(S(C)(=O)=O)=C1 BRDKHBSREKWDRJ-GKOSEXJESA-N 0.000 claims 1
- ABJRGQFLFPDONJ-GKOSEXJESA-N [2H]C([2H])([2H])OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCC(C)(C)OC3=N2)=NC(S(C)(=O)=O)=C1 Chemical compound [2H]C([2H])([2H])OC1=CC(NC2=CC(NC(C)=O)=NC=C2C2=CC=C3OCC(C)(C)OC3=N2)=NC(S(C)(=O)=O)=C1 ABJRGQFLFPDONJ-GKOSEXJESA-N 0.000 claims 1
- 102100032028 Non-receptor tyrosine-protein kinase TYK2 Human genes 0.000 abstract description 11
- 101000844245 Homo sapiens Non-receptor tyrosine-protein kinase TYK2 Proteins 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 387
- 239000000243 solution Substances 0.000 description 208
- 239000000047 product Substances 0.000 description 150
- 239000004698 Polyethylene Substances 0.000 description 146
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
- 239000012044 organic layer Substances 0.000 description 136
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 133
- 230000015572 biosynthetic process Effects 0.000 description 131
- 238000003786 synthesis reaction Methods 0.000 description 127
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 125
- 239000011734 sodium Substances 0.000 description 125
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 113
- 238000005160 1H NMR spectroscopy Methods 0.000 description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 101
- 238000006243 chemical reaction Methods 0.000 description 85
- 239000012267 brine Substances 0.000 description 83
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 83
- 239000000706 filtrate Substances 0.000 description 79
- 238000001914 filtration Methods 0.000 description 72
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 72
- 235000019439 ethyl acetate Nutrition 0.000 description 69
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 63
- 239000002904 solvent Substances 0.000 description 56
- 239000012299 nitrogen atmosphere Substances 0.000 description 51
- 238000004809 thin layer chromatography Methods 0.000 description 51
- 230000002829 reductive effect Effects 0.000 description 44
- 241000872931 Myoporum sandwicense Species 0.000 description 40
- 239000012043 crude product Substances 0.000 description 32
- 238000000746 purification Methods 0.000 description 28
- 125000005843 halogen group Chemical group 0.000 description 27
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 23
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- SBYMOWYNFFJYLP-UHFFFAOYSA-N 2-bromo-6-methylsulfonyl-1H-pyridin-4-one Chemical compound CS(C1=CC(O)=CC(Br)=N1)(=O)=O SBYMOWYNFFJYLP-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 238000010898 silica gel chromatography Methods 0.000 description 20
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 19
- 125000002950 monocyclic group Chemical group 0.000 description 18
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 239000012298 atmosphere Substances 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- QBAVTOCDJMSXDH-TXEJJXNPSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1N Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(NC(C)=O)=C1)=C1N QBAVTOCDJMSXDH-TXEJJXNPSA-N 0.000 description 10
- 208000035475 disorder Diseases 0.000 description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- PZFMWYNHJFZBPO-UHFFFAOYSA-N 3,5-dibromophenol Chemical compound OC1=CC(Br)=CC(Br)=C1 PZFMWYNHJFZBPO-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 7
- 239000012258 stirred mixture Substances 0.000 description 7
- NGSKFMPSBUAUNE-UHFFFAOYSA-N 2,6-dichloro-4-iodopyridine Chemical compound ClC1=CC(I)=CC(Cl)=N1 NGSKFMPSBUAUNE-UHFFFAOYSA-N 0.000 description 6
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 6
- XYCDTWLSFLCPEZ-UHFFFAOYSA-N CC(NC(N=C1)=CC(N)=C1C(C=C1)=NC=C1F)=O Chemical compound CC(NC(N=C1)=CC(N)=C1C(C=C1)=NC=C1F)=O XYCDTWLSFLCPEZ-UHFFFAOYSA-N 0.000 description 6
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 description 6
- XOGTZOOQQBDUSI-UHFFFAOYSA-M Mesna Chemical compound [Na+].[O-]S(=O)(=O)CCS XOGTZOOQQBDUSI-UHFFFAOYSA-M 0.000 description 6
- 108010010057 TYK2 Kinase Proteins 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229960004635 mesna Drugs 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- FGDIUEDAZXIZBM-UHFFFAOYSA-N 2,6-dibromo-1h-pyridin-4-one Chemical compound BrC1=CC(=O)C=C(Br)N1 FGDIUEDAZXIZBM-UHFFFAOYSA-N 0.000 description 5
- OCPAOWKPPOLAJU-UHFFFAOYSA-N 2-bromo-4-methyl-6-methylsulfonylpyridine Chemical compound CC1=CC(Br)=NC(S(C)(=O)=O)=C1 OCPAOWKPPOLAJU-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 238000002953 preparative HPLC Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- YHPRZESYFBZNHD-UHFFFAOYSA-N 2-bromo-4-(1-methoxyethyl)-6-methylsulfonylpyridine Chemical compound CC(C1=CC(Br)=NC(S(C)(=O)=O)=C1)OC YHPRZESYFBZNHD-UHFFFAOYSA-N 0.000 description 4
- CVWZBJNPVDMYKB-UHFFFAOYSA-N 2-bromo-6-iodo-3-methoxy-1h-pyridin-4-one Chemical compound COC1=C(Br)NC(I)=CC1=O CVWZBJNPVDMYKB-UHFFFAOYSA-N 0.000 description 4
- LHDNVVCKJSWJKM-UHFFFAOYSA-N 2-bromo-6-iodo-3-methoxypyridine Chemical compound COC1=CC=C(I)N=C1Br LHDNVVCKJSWJKM-UHFFFAOYSA-N 0.000 description 4
- XKDRUGUIPVWKAM-FIBGUPNXSA-N 2-bromo-6-methylsulfonyl-4-(trideuteriomethoxy)pyridine Chemical compound [2H]C([2H])([2H])OC1=CC(Br)=NC(S(C)(=O)=O)=C1 XKDRUGUIPVWKAM-FIBGUPNXSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- UDJHTGSHJMSPRJ-UHFFFAOYSA-N 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN=C(N)C=C1Cl UDJHTGSHJMSPRJ-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- WTJIHLBKIFBHOK-UHFFFAOYSA-N CC(NC1=NC=C(C2=CC=CN=N2)C(Cl)=C1)=O Chemical compound CC(NC1=NC=C(C2=CC=CN=N2)C(Cl)=C1)=O WTJIHLBKIFBHOK-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 108010024121 Janus Kinases Proteins 0.000 description 4
- 102000015617 Janus Kinases Human genes 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 3
- JIWVWYSMIOTTFP-UHFFFAOYSA-N 2,6-dibromo-4-(bromomethyl)pyridine Chemical compound BrCC1=CC(Br)=NC(Br)=C1 JIWVWYSMIOTTFP-UHFFFAOYSA-N 0.000 description 3
- JDDYTJYVMUKUPJ-UHFFFAOYSA-N 2,6-dibromo-4-(methoxymethyl)pyridine Chemical compound BrC1=NC(=CC(=C1)COC)Br JDDYTJYVMUKUPJ-UHFFFAOYSA-N 0.000 description 3
- RPLWQERFYBEHLW-UHFFFAOYSA-N 2,6-dibromo-4-iodopyridine Chemical compound BrC1=CC(I)=CC(Br)=N1 RPLWQERFYBEHLW-UHFFFAOYSA-N 0.000 description 3
- OHBIPNNTWKNAGC-UHFFFAOYSA-N 2,6-dibromo-4-methylpyridine Chemical compound CC1=CC(Br)=NC(Br)=C1 OHBIPNNTWKNAGC-UHFFFAOYSA-N 0.000 description 3
- LMFFGAUQSWOBOS-UHFFFAOYSA-N 2,6-dibromo-4-phenylpyridine Chemical compound BrC1=NC(Br)=CC(C=2C=CC=CC=2)=C1 LMFFGAUQSWOBOS-UHFFFAOYSA-N 0.000 description 3
- RTSGMUHVJLAAAU-UHFFFAOYSA-N 2-(2-chloroethoxy)acetyl chloride Chemical compound ClCCOCC(Cl)=O RTSGMUHVJLAAAU-UHFFFAOYSA-N 0.000 description 3
- XMIALDWLRAIBML-UHFFFAOYSA-N 2-[(5-iodoimidazol-1-yl)methoxy]ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCN1C=NC=C1I XMIALDWLRAIBML-UHFFFAOYSA-N 0.000 description 3
- HMCVIJRMPYIMTO-UHFFFAOYSA-N 2-bromo-3-(difluoromethoxy)-6-iodopyridine Chemical compound FC(F)OC1=CC=C(I)N=C1Br HMCVIJRMPYIMTO-UHFFFAOYSA-N 0.000 description 3
- GAPRDCJLVSZWQW-UHFFFAOYSA-N 2-bromo-3-(difluoromethoxy)-6-methylsulfanylpyridine Chemical compound CSC(N=C1Br)=CC=C1OC(F)F GAPRDCJLVSZWQW-UHFFFAOYSA-N 0.000 description 3
- BKBGCLIFPLBTKB-UHFFFAOYSA-N 2-bromo-3-(difluoromethoxy)-6-methylsulfonylpyridine Chemical compound CS(C(N=C1Br)=CC=C1OC(F)F)(=O)=O BKBGCLIFPLBTKB-UHFFFAOYSA-N 0.000 description 3
- LVRGZNCYCQFUAB-UHFFFAOYSA-N 2-bromo-4-(methoxymethyl)-6-methylsulfanylpyridine Chemical compound COCC1=CC(Br)=NC(SC)=C1 LVRGZNCYCQFUAB-UHFFFAOYSA-N 0.000 description 3
- PYLUCWGAULCIAG-UHFFFAOYSA-N 2-bromo-4-(methoxymethyl)-6-methylsulfonylpyridine Chemical compound COCC1=CC(Br)=NC(S(C)(=O)=O)=C1 PYLUCWGAULCIAG-UHFFFAOYSA-N 0.000 description 3
- XKDRUGUIPVWKAM-UHFFFAOYSA-N 2-bromo-4-methoxy-6-methylsulfonylpyridine Chemical compound COC1=CC(Br)=NC(S(C)(=O)=O)=C1 XKDRUGUIPVWKAM-UHFFFAOYSA-N 0.000 description 3
- QMNYDLUNGKGNLV-UHFFFAOYSA-N 2-bromo-5-(2-methoxyethoxy)pyridine Chemical compound COCCOC1=CC=C(Br)N=C1 QMNYDLUNGKGNLV-UHFFFAOYSA-N 0.000 description 3
- VYADQLKEISKNDT-UHFFFAOYSA-N 2-bromo-5-(methoxymethyl)pyridine Chemical compound COCC1=CC=C(Br)N=C1 VYADQLKEISKNDT-UHFFFAOYSA-N 0.000 description 3
- YJRQJULOXMNBIY-UHFFFAOYSA-N 2-bromo-6-ethylsulfanyl-1H-pyridin-4-one Chemical compound CCSC1=CC(O)=CC(Br)=N1 YJRQJULOXMNBIY-UHFFFAOYSA-N 0.000 description 3
- KVKHJZMVBIPSAM-UHFFFAOYSA-N 2-bromo-6-ethylsulfonyl-1H-pyridin-4-one Chemical compound CCS(C1=CC(O)=CC(Br)=N1)(=O)=O KVKHJZMVBIPSAM-UHFFFAOYSA-N 0.000 description 3
- JWBQUGVCUQMEDC-UHFFFAOYSA-N 2-bromo-6-ethylsulfonyl-4-propan-2-yloxypyridine Chemical compound CCS(C1=CC(OC(C)C)=CC(Br)=N1)(=O)=O JWBQUGVCUQMEDC-UHFFFAOYSA-N 0.000 description 3
- IQUADFAYJOJQJA-UHFFFAOYSA-N 2-bromo-6-iodopyridin-3-ol Chemical compound OC1=CC=C(I)N=C1Br IQUADFAYJOJQJA-UHFFFAOYSA-N 0.000 description 3
- BHVCNSIGYOFAJA-UHFFFAOYSA-N 2-bromo-6-methylsulfanyl-1H-pyridin-4-one Chemical compound CSC1=CC(O)=CC(Br)=N1 BHVCNSIGYOFAJA-UHFFFAOYSA-N 0.000 description 3
- XZERGEGHRQPMMW-UHFFFAOYSA-N 2-bromo-6-methylsulfonyl-4-(oxan-4-yl)pyridine Chemical compound CS(C1=CC(C2CCOCC2)=CC(Br)=N1)(=O)=O XZERGEGHRQPMMW-UHFFFAOYSA-N 0.000 description 3
- UFSQJRPUTARKCG-UHFFFAOYSA-N 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-amine Chemical compound CC1(C)OB(OC1(C)C)c1cnc(Cl)cc1N UFSQJRPUTARKCG-UHFFFAOYSA-N 0.000 description 3
- MBNPJRQKQLLRIS-UHFFFAOYSA-N 3-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=CC(N)=C1 MBNPJRQKQLLRIS-UHFFFAOYSA-N 0.000 description 3
- JRUVBCJFROXRLE-UHFFFAOYSA-N 4-(6-bromopyridin-3-yl)morpholin-3-one Chemical compound C1=NC(Br)=CC=C1N1C(=O)COCC1 JRUVBCJFROXRLE-UHFFFAOYSA-N 0.000 description 3
- WAHHMDDMGAFUBO-UHFFFAOYSA-N 5-bromo-2-chloro-N-(3-methylsulfonylphenyl)pyridin-4-amine Chemical compound CS(C1=CC=CC(NC2=CC(Cl)=NC=C2Br)=C1)(=O)=O WAHHMDDMGAFUBO-UHFFFAOYSA-N 0.000 description 3
- UIFQXJXLYDLHEV-UHFFFAOYSA-N 6-bromo-4-(2-methoxyethoxy)pyridine-2-sulfonyl chloride Chemical compound COCCOC1=CC(S(Cl)(=O)=O)=NC(Br)=C1 UIFQXJXLYDLHEV-UHFFFAOYSA-N 0.000 description 3
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 3
- ZWLADZJFRIBMHI-UHFFFAOYSA-N BrC1=NC(I)=CC2=C1OCCO2 Chemical compound BrC1=NC(I)=CC2=C1OCCO2 ZWLADZJFRIBMHI-UHFFFAOYSA-N 0.000 description 3
- WPPDRGKXLPYLRJ-UHFFFAOYSA-N CC(CC1)(CCN1C1=CC(Br)=NC(Br)=C1)O Chemical compound CC(CC1)(CCN1C1=CC(Br)=NC(Br)=C1)O WPPDRGKXLPYLRJ-UHFFFAOYSA-N 0.000 description 3
- YEISKGNXDKTREU-UHFFFAOYSA-N CC(CC1)(CCN1C1=CC(Br)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(CC1)(CCN1C1=CC(Br)=NC(S(C)(=O)=O)=C1)O YEISKGNXDKTREU-UHFFFAOYSA-N 0.000 description 3
- JFFQXWHDQRZCOJ-UHFFFAOYSA-N CC(CC1)(CCN1C1=CC(Br)=NC(SC)=C1)O Chemical compound CC(CC1)(CCN1C1=CC(Br)=NC(SC)=C1)O JFFQXWHDQRZCOJ-UHFFFAOYSA-N 0.000 description 3
- BLPHLTAHUSJQNF-UHFFFAOYSA-N CC(COC1=CC(Br)=NC(S(C)(=O)=O)=C1)O Chemical compound CC(COC1=CC(Br)=NC(S(C)(=O)=O)=C1)O BLPHLTAHUSJQNF-UHFFFAOYSA-N 0.000 description 3
- LGYKMVXJENLHCD-UHFFFAOYSA-N CC(COC1=CC(Br)=NC(S(C)(=O)=O)=C1)O[Si](C)(C)C(C)(C)C Chemical compound CC(COC1=CC(Br)=NC(S(C)(=O)=O)=C1)O[Si](C)(C)C(C)(C)C LGYKMVXJENLHCD-UHFFFAOYSA-N 0.000 description 3
- RNPLPBJWLRQNRF-UHFFFAOYSA-N CC(NC(N=C1)=CC(Cl)=C1C(C=C1)=NC=C1N(CCOC1)C1=O)=O Chemical compound CC(NC(N=C1)=CC(Cl)=C1C(C=C1)=NC=C1N(CCOC1)C1=O)=O RNPLPBJWLRQNRF-UHFFFAOYSA-N 0.000 description 3
- RYDZRJCNFWEOQE-UHFFFAOYSA-N CC(NC(N=C1)=CC(N)=C1C(C=C1)=NC=C1OCCOC)=O Chemical compound CC(NC(N=C1)=CC(N)=C1C(C=C1)=NC=C1OCCOC)=O RYDZRJCNFWEOQE-UHFFFAOYSA-N 0.000 description 3
- QOYHEUWGZQOWMC-UHFFFAOYSA-N CC(NC(N=C1)=CC(N)=C1C1=NC=CC=C1)=O Chemical compound CC(NC(N=C1)=CC(N)=C1C1=NC=CC=C1)=O QOYHEUWGZQOWMC-UHFFFAOYSA-N 0.000 description 3
- IOCAFJDWMRTYQM-UHFFFAOYSA-N COC(C=C(N=C1Br)S(C)(=O)=O)=C1OC Chemical compound COC(C=C(N=C1Br)S(C)(=O)=O)=C1OC IOCAFJDWMRTYQM-UHFFFAOYSA-N 0.000 description 3
- ZYNOOISOGKKLKA-UHFFFAOYSA-N COC1=CC=C(CNC(C=C2NC3=CC(S(C)(=O)=O)=CC=C3)=NC=C2Br)C=C1 Chemical compound COC1=CC=C(CNC(C=C2NC3=CC(S(C)(=O)=O)=CC=C3)=NC=C2Br)C=C1 ZYNOOISOGKKLKA-UHFFFAOYSA-N 0.000 description 3
- MUPZZBJFVJSBSM-UHFFFAOYSA-N CS(C(N=C1Br)=CC2=C1OCCO2)(=O)=O Chemical compound CS(C(N=C1Br)=CC2=C1OCCO2)(=O)=O MUPZZBJFVJSBSM-UHFFFAOYSA-N 0.000 description 3
- PCFSNRISOQFXOV-UHFFFAOYSA-N CS(C1=CC(C2OCCOC2)=CC(Cl)=N1)(=O)=O Chemical compound CS(C1=CC(C2OCCOC2)=CC(Cl)=N1)(=O)=O PCFSNRISOQFXOV-UHFFFAOYSA-N 0.000 description 3
- CEXGRHUELHPTNV-NSHDSACASA-N C[C@@H](COC1=CC(Br)=CC(Br)=C1)O[Si](C)(C)C(C)(C)C Chemical compound C[C@@H](COC1=CC(Br)=CC(Br)=C1)O[Si](C)(C)C(C)(C)C CEXGRHUELHPTNV-NSHDSACASA-N 0.000 description 3
- YDBNBBVHEUIOSY-LBPRGKRZSA-N C[C@@H](COC1=CC(Br)=CC(S(C)(=O)=O)=C1)O[Si](C)(C)C(C)(C)C Chemical compound C[C@@H](COC1=CC(Br)=CC(S(C)(=O)=O)=C1)O[Si](C)(C)C(C)(C)C YDBNBBVHEUIOSY-LBPRGKRZSA-N 0.000 description 3
- JTKWRYPCFPIPSY-LBPRGKRZSA-N C[C@@H](COC1=CC(Br)=CC(SC)=C1)O[Si](C)(C)C(C)(C)C Chemical compound C[C@@H](COC1=CC(Br)=CC(SC)=C1)O[Si](C)(C)C(C)(C)C JTKWRYPCFPIPSY-LBPRGKRZSA-N 0.000 description 3
- RJPSIKKOTAMAOE-QMMMGPOBSA-N C[C@@H](COCC1)N1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 Chemical compound C[C@@H](COCC1)N1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 RJPSIKKOTAMAOE-QMMMGPOBSA-N 0.000 description 3
- KCOHSPXAPGPZJZ-PHIMTYICSA-N C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(Cl)=C1)=C1N Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=C1)=CN=C1C(C=NC(Cl)=C1)=C1N KCOHSPXAPGPZJZ-PHIMTYICSA-N 0.000 description 3
- YDBNBBVHEUIOSY-GFCCVEGCSA-N C[C@H](COC1=CC(Br)=CC(S(C)(=O)=O)=C1)O[Si](C)(C)C(C)(C)C Chemical compound C[C@H](COC1=CC(Br)=CC(S(C)(=O)=O)=C1)O[Si](C)(C)C(C)(C)C YDBNBBVHEUIOSY-GFCCVEGCSA-N 0.000 description 3
- RRPCJKYMAZFBMU-ZCFIWIBFSA-N C[C@H](COC1=CC(Br)=NC(Br)=C1)OC Chemical compound C[C@H](COC1=CC(Br)=NC(Br)=C1)OC RRPCJKYMAZFBMU-ZCFIWIBFSA-N 0.000 description 3
- RQSYAOVZASZTIO-SSDOTTSWSA-N C[C@H](COC1=CC(Br)=NC(S(C)(=O)=O)=C1)OC Chemical compound C[C@H](COC1=CC(Br)=NC(S(C)(=O)=O)=C1)OC RQSYAOVZASZTIO-SSDOTTSWSA-N 0.000 description 3
- JTCHVEDQICOZQQ-SSDOTTSWSA-N C[C@H](COC1=CC(Br)=NC(SC)=C1)OC Chemical compound C[C@H](COC1=CC(Br)=NC(SC)=C1)OC JTCHVEDQICOZQQ-SSDOTTSWSA-N 0.000 description 3
- RJPSIKKOTAMAOE-MRVPVSSYSA-N C[C@H](COCC1)N1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 Chemical compound C[C@H](COCC1)N1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 RJPSIKKOTAMAOE-MRVPVSSYSA-N 0.000 description 3
- WPUIJQXVEYLYGG-UHFFFAOYSA-N C[Si](C)(C)CCOCN1C(C(C(N)=C2)=CN=C2Cl)=CN=C1 Chemical compound C[Si](C)(C)CCOCN1C(C(C(N)=C2)=CN=C2Cl)=CN=C1 WPUIJQXVEYLYGG-UHFFFAOYSA-N 0.000 description 3
- ISCFLIAFMDFTNI-UHFFFAOYSA-N C[Si](C)(C)CCOCN1C=NC(C(C(N)=C2)=CN=C2Cl)=C1 Chemical compound C[Si](C)(C)CCOCN1C=NC(C(C(N)=C2)=CN=C2Cl)=C1 ISCFLIAFMDFTNI-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 description 3
- DTHCKABVHNKXPY-UHFFFAOYSA-N NC(N=C1)=CC(Cl)=C1C(C=C1)=NC=C1N(CCOC1)C1=O Chemical compound NC(N=C1)=CC(Cl)=C1C(C=C1)=NC=C1N(CCOC1)C1=O DTHCKABVHNKXPY-UHFFFAOYSA-N 0.000 description 3
- QBUGFHVOFGTNNM-UHFFFAOYSA-N OC(C=C(N=C1Br)I)=C1O Chemical compound OC(C=C(N=C1Br)I)=C1O QBUGFHVOFGTNNM-UHFFFAOYSA-N 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 239000004012 Tofacitinib Substances 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 description 3
- ZRLDVMGSMOLUOJ-SECBINFHSA-N [(2r)-2-hydroxypropyl] 4-methylbenzenesulfonate Chemical compound C[C@@H](O)COS(=O)(=O)C1=CC=C(C)C=C1 ZRLDVMGSMOLUOJ-SECBINFHSA-N 0.000 description 3
- IHRUWHJSVMOZTQ-SNVBAGLBSA-N [(2r)-2-methoxypropyl] 4-methylbenzenesulfonate Chemical compound CO[C@H](C)COS(=O)(=O)C1=CC=C(C)C=C1 IHRUWHJSVMOZTQ-SNVBAGLBSA-N 0.000 description 3
- ZRLDVMGSMOLUOJ-VIFPVBQESA-N [(2s)-2-hydroxypropyl] 4-methylbenzenesulfonate Chemical compound C[C@H](O)COS(=O)(=O)C1=CC=C(C)C=C1 ZRLDVMGSMOLUOJ-VIFPVBQESA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- PLBRYXAUQUCSOP-UHFFFAOYSA-N n-(6-bromopyridin-3-yl)-2-(2-chloroethoxy)acetamide Chemical compound ClCCOCC(=O)NC1=CC=C(Br)N=C1 PLBRYXAUQUCSOP-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
- 229960001350 tofacitinib Drugs 0.000 description 3
- UJLAWZDWDVHWOW-YPMHNXCESA-N tofacitinib Chemical compound C[C@@H]1CCN(C(=O)CC#N)C[C@@H]1N(C)C1=NC=NC2=C1C=CN2 UJLAWZDWDVHWOW-YPMHNXCESA-N 0.000 description 3
- 238000013518 transcription Methods 0.000 description 3
- 230000035897 transcription Effects 0.000 description 3
- YYJODMMTPSDERD-UHFFFAOYSA-N (2,6-dibromopyridin-4-yl)methanol Chemical compound OCC1=CC(Br)=NC(Br)=C1 YYJODMMTPSDERD-UHFFFAOYSA-N 0.000 description 2
- SOHNHMPRMJKRJT-SSDOTTSWSA-N (3R)-4-(2,6-dichloropyridin-4-yl)-3-methylmorpholine Chemical compound ClC1=NC(=CC(=C1)N1[C@@H](COCC1)C)Cl SOHNHMPRMJKRJT-SSDOTTSWSA-N 0.000 description 2
- DTDJRWPAPDWXAC-UHFFFAOYSA-N 1,3-dibromo-5-(2-methoxyethoxy)benzene Chemical compound COCCOC1=CC(Br)=CC(Br)=C1 DTDJRWPAPDWXAC-UHFFFAOYSA-N 0.000 description 2
- GHEAEHMLHSSQNK-UHFFFAOYSA-N 1,3-dibromo-5-(cyclopropylmethoxy)benzene Chemical compound BrC1=CC(Br)=CC(OCC2CC2)=C1 GHEAEHMLHSSQNK-UHFFFAOYSA-N 0.000 description 2
- BDXVIFKJOCEBOR-UHFFFAOYSA-N 1,3-dibromo-5-(methoxymethyl)benzene Chemical compound COCC1=CC(Br)=CC(Br)=C1 BDXVIFKJOCEBOR-UHFFFAOYSA-N 0.000 description 2
- UQXCWJRIRDBDIA-UHFFFAOYSA-N 1,3-dibromo-5-cyclopropyloxybenzene Chemical compound BrC1=CC(=CC(=C1)OC1CC1)Br UQXCWJRIRDBDIA-UHFFFAOYSA-N 0.000 description 2
- YEANGEKXRPNJTL-UHFFFAOYSA-N 1,3-dibromo-5-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC(Br)=CC(Br)=C1 YEANGEKXRPNJTL-UHFFFAOYSA-N 0.000 description 2
- LDJUSQFASVHMJC-UHFFFAOYSA-N 1-(2,6-dibromopyridin-4-yl)ethanol Chemical compound CC(O)C1=CC(Br)=NC(Br)=C1 LDJUSQFASVHMJC-UHFFFAOYSA-N 0.000 description 2
- GOSRHYMWNMKGBR-UHFFFAOYSA-N 1-(2,6-dibromopyridin-4-yl)ethanone Chemical compound CC(=O)C1=CC(Br)=NC(Br)=C1 GOSRHYMWNMKGBR-UHFFFAOYSA-N 0.000 description 2
- XCJCXUOEYWAEKR-UHFFFAOYSA-N 1-(2,6-dichloropyridin-4-yl)-3-phenylmethoxycyclobutane-1-carbonitrile Chemical compound N#CC(C1)(CC1OCC1=CC=CC=C1)C1=CC(Cl)=NC(Cl)=C1 XCJCXUOEYWAEKR-UHFFFAOYSA-N 0.000 description 2
- XVSDLWLPWJRBMC-UHFFFAOYSA-N 1-(2,6-dichloropyridin-4-yl)ethanol Chemical compound CC(O)C1=CC(Cl)=NC(Cl)=C1 XVSDLWLPWJRBMC-UHFFFAOYSA-N 0.000 description 2
- FSDUERRXWQQHIF-UHFFFAOYSA-N 1-bromo-3-(2-methoxyethoxy)-5-methylsulfanylbenzene Chemical compound COCCOC1=CC(SC)=CC(Br)=C1 FSDUERRXWQQHIF-UHFFFAOYSA-N 0.000 description 2
- KCGYBOOSMRWRHZ-UHFFFAOYSA-N 1-bromo-3-(2-methoxyethoxy)-5-methylsulfonylbenzene Chemical compound COCCOC1=CC(Br)=CC(S(C)(=O)=O)=C1 KCGYBOOSMRWRHZ-UHFFFAOYSA-N 0.000 description 2
- DNVNRTSTRHULKA-UHFFFAOYSA-N 1-bromo-3-(cyclopropylmethoxy)-5-methylsulfanylbenzene Chemical compound CSC1=CC(Br)=CC(OCC2CC2)=C1 DNVNRTSTRHULKA-UHFFFAOYSA-N 0.000 description 2
- BOAGTVRLVKXHSU-UHFFFAOYSA-N 1-bromo-3-(cyclopropylmethoxy)-5-methylsulfonylbenzene Chemical compound CS(C1=CC(Br)=CC(OCC2CC2)=C1)(=O)=O BOAGTVRLVKXHSU-UHFFFAOYSA-N 0.000 description 2
- FFZHMDNVCLCNAA-UHFFFAOYSA-N 1-bromo-3-(difluoromethyl)-5-methylsulfanylbenzene Chemical compound CSC1=CC(Br)=CC(C(F)F)=C1 FFZHMDNVCLCNAA-UHFFFAOYSA-N 0.000 description 2
- LKFYOUNAMBYWHG-UHFFFAOYSA-N 1-bromo-3-(difluoromethyl)-5-methylsulfonylbenzene Chemical compound CS(C1=CC(Br)=CC(C(F)F)=C1)(=O)=O LKFYOUNAMBYWHG-UHFFFAOYSA-N 0.000 description 2
- YYDKWPLEVSWJLJ-UHFFFAOYSA-N 1-bromo-3-(methoxymethyl)-5-methylsulfanylbenzene Chemical compound COCC1=CC(SC)=CC(Br)=C1 YYDKWPLEVSWJLJ-UHFFFAOYSA-N 0.000 description 2
- FYBJGOSBTXWBAV-UHFFFAOYSA-N 1-bromo-3-(methoxymethyl)-5-methylsulfonylbenzene Chemical compound COCC1=CC(Br)=CC(S(C)(=O)=O)=C1 FYBJGOSBTXWBAV-UHFFFAOYSA-N 0.000 description 2
- CCMUSMZCVAPTEC-UHFFFAOYSA-N 1-bromo-3-chloro-5-methylsulfanylbenzene Chemical compound CSC1=CC(Cl)=CC(Br)=C1 CCMUSMZCVAPTEC-UHFFFAOYSA-N 0.000 description 2
- VWQJEFABVOZLAS-UHFFFAOYSA-N 1-bromo-3-chloro-5-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC(Cl)=CC(Br)=C1 VWQJEFABVOZLAS-UHFFFAOYSA-N 0.000 description 2
- JIIHESLLWFSMQC-UHFFFAOYSA-N 1-bromo-3-cyclopropyloxy-5-methylsulfanylbenzene Chemical compound CSC1=CC(Br)=CC(OC2CC2)=C1 JIIHESLLWFSMQC-UHFFFAOYSA-N 0.000 description 2
- KEVITNKJQWCSIG-UHFFFAOYSA-N 1-bromo-3-cyclopropyloxy-5-methylsulfonylbenzene Chemical compound CS(C1=CC(Br)=CC(OC2CC2)=C1)(=O)=O KEVITNKJQWCSIG-UHFFFAOYSA-N 0.000 description 2
- UGPADPFJPFQOKT-UHFFFAOYSA-N 1-bromo-3-fluoro-5-methylsulfanylbenzene Chemical compound CSC1=CC(F)=CC(Br)=C1 UGPADPFJPFQOKT-UHFFFAOYSA-N 0.000 description 2
- MUZWOUMGPHLUOY-UHFFFAOYSA-N 1-bromo-3-fluoro-5-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC(F)=CC(Br)=C1 MUZWOUMGPHLUOY-UHFFFAOYSA-N 0.000 description 2
- UYMLMWBJVXOHRJ-UHFFFAOYSA-N 1-bromo-3-methoxy-5-methylsulfanylbenzene Chemical compound COc1cc(Br)cc(SC)c1 UYMLMWBJVXOHRJ-UHFFFAOYSA-N 0.000 description 2
- ULOODDSURQASHD-UHFFFAOYSA-N 1-bromo-3-methoxy-5-methylsulfonylbenzene Chemical compound COC1=CC(S(C)(=O)=O)=CC(Br)=C1 ULOODDSURQASHD-UHFFFAOYSA-N 0.000 description 2
- VYWHSTJRGXYWCE-UHFFFAOYSA-N 1-bromo-3-methyl-5-methylsulfanylbenzene Chemical compound CSc1cc(C)cc(Br)c1 VYWHSTJRGXYWCE-UHFFFAOYSA-N 0.000 description 2
- VLFFSTHAVZZFJO-UHFFFAOYSA-N 1-bromo-3-methyl-5-methylsulfonylbenzene Chemical compound CC1=CC(Br)=CC(S(C)(=O)=O)=C1 VLFFSTHAVZZFJO-UHFFFAOYSA-N 0.000 description 2
- PERYEEDVHXPNOQ-UHFFFAOYSA-N 1-bromo-3-methylsulfanyl-5-(trifluoromethoxy)benzene Chemical compound CSC1=CC(OC(F)(F)F)=CC(Br)=C1 PERYEEDVHXPNOQ-UHFFFAOYSA-N 0.000 description 2
- CJURJMLJGPQJAO-UHFFFAOYSA-N 1-bromo-3-methylsulfanyl-5-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC(SC)=CC(Br)=C1 CJURJMLJGPQJAO-UHFFFAOYSA-N 0.000 description 2
- FSWYUXOCSSZCHW-UHFFFAOYSA-N 1-bromo-3-methylsulfonyl-5-(trifluoromethoxy)benzene Chemical compound CS(C1=CC(OC(F)(F)F)=CC(Br)=C1)(=O)=O FSWYUXOCSSZCHW-UHFFFAOYSA-N 0.000 description 2
- OAMTXMGOIJYKOL-UHFFFAOYSA-N 1-bromo-3-methylsulfonyl-5-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC(S(C)(=O)=O)=CC(Br)=C1 OAMTXMGOIJYKOL-UHFFFAOYSA-N 0.000 description 2
- WBOMXUMQOVQNKT-UHFFFAOYSA-N 1-bromo-3-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC(Br)=C1 WBOMXUMQOVQNKT-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- GBVWUOOPHOZKHQ-UHFFFAOYSA-N 2,6-dibromo-4-(2-methoxyethoxy)pyridine Chemical compound COCCOC1=CC(Br)=NC(Br)=C1 GBVWUOOPHOZKHQ-UHFFFAOYSA-N 0.000 description 2
- SUXPXTUYNMILLJ-UHFFFAOYSA-N 2,6-dibromo-4-(difluoromethyl)pyridine Chemical compound FC(F)c1cc(Br)nc(Br)c1 SUXPXTUYNMILLJ-UHFFFAOYSA-N 0.000 description 2
- NPWNLINKWYZTFY-UHFFFAOYSA-N 2,6-dibromo-n-methoxy-n-methylpyridine-4-carboxamide Chemical compound CON(C)C(=O)C1=CC(Br)=NC(Br)=C1 NPWNLINKWYZTFY-UHFFFAOYSA-N 0.000 description 2
- OVMDNAWSEWSGDV-UHFFFAOYSA-N 2,6-dibromopyridine-4-carbaldehyde Chemical compound BrC1=CC(C=O)=CC(Br)=N1 OVMDNAWSEWSGDV-UHFFFAOYSA-N 0.000 description 2
- AULQTVXAKNKCCA-UHFFFAOYSA-N 2,6-dibromopyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC(Br)=NC(Br)=C1 AULQTVXAKNKCCA-UHFFFAOYSA-N 0.000 description 2
- YKZYQJPJDHKVHX-UHFFFAOYSA-N 2,6-dichloro-4-ethenylpyridine Chemical compound ClC1=CC(C=C)=CC(Cl)=N1 YKZYQJPJDHKVHX-UHFFFAOYSA-N 0.000 description 2
- SCKJGQVWDLYKGZ-UHFFFAOYSA-N 2-(6-bromo-4-iodopyridin-3-yl)oxyethanol Chemical compound BrC1=CC(=C(C=N1)OCCO)I SCKJGQVWDLYKGZ-UHFFFAOYSA-N 0.000 description 2
- BVOHFHIEDQSTKD-UHFFFAOYSA-N 2-[(4-iodoimidazol-1-yl)methoxy]ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCN1C=NC(I)=C1 BVOHFHIEDQSTKD-UHFFFAOYSA-N 0.000 description 2
- WKSLDAYGGXZBDT-UHFFFAOYSA-N 2-benzylsulfanyl-6-bromo-4-methylpyridine Chemical compound CC1=CC(SCC2=CC=CC=C2)=NC(Br)=C1 WKSLDAYGGXZBDT-UHFFFAOYSA-N 0.000 description 2
- LORJMVIUVFJSNL-UHFFFAOYSA-N 2-bromo-3-methoxy-6-methylsulfanylpyridine Chemical compound COC(C(Br)=N1)=CC=C1SC LORJMVIUVFJSNL-UHFFFAOYSA-N 0.000 description 2
- FINUEDAJSKYYLI-UHFFFAOYSA-N 2-bromo-3-methoxy-6-methylsulfonylpyridine Chemical compound COC(C(Br)=N1)=CC=C1S(C)(=O)=O FINUEDAJSKYYLI-UHFFFAOYSA-N 0.000 description 2
- XEZOWGQWQJODTP-UHFFFAOYSA-N 2-bromo-4-(1-methoxyethyl)-6-methylsulfanylpyridine Chemical compound CC(C1=CC(Br)=NC(SC)=C1)OC XEZOWGQWQJODTP-UHFFFAOYSA-N 0.000 description 2
- RCRKACWRIJVAHR-UHFFFAOYSA-N 2-bromo-4-(2-methylpropoxy)-6-methylsulfonylpyridine Chemical compound CC(C)COC1=CC(Br)=NC(S(C)(=O)=O)=C1 RCRKACWRIJVAHR-UHFFFAOYSA-N 0.000 description 2
- SXXGJOGWCVTFEG-UHFFFAOYSA-N 2-bromo-4-(cyclopropylmethoxy)-6-methylsulfonylpyridine Chemical compound CS(C1=CC(OCC2CC2)=CC(Br)=N1)(=O)=O SXXGJOGWCVTFEG-UHFFFAOYSA-N 0.000 description 2
- WWOINWBDPFYXFM-UHFFFAOYSA-N 2-bromo-4-(difluoromethoxy)-6-methylsulfonylpyridine Chemical compound CS(C1=CC(OC(F)F)=CC(Br)=N1)(=O)=O WWOINWBDPFYXFM-UHFFFAOYSA-N 0.000 description 2
- HUFZXFBSAJXKIM-UHFFFAOYSA-N 2-bromo-4-(difluoromethyl)-6-methylsulfanylpyridine Chemical compound CSC1=CC(C(F)F)=CC(Br)=N1 HUFZXFBSAJXKIM-UHFFFAOYSA-N 0.000 description 2
- SNDGKBMVZALTTE-UHFFFAOYSA-N 2-bromo-4-(difluoromethyl)-6-methylsulfonylpyridine Chemical compound CS(C1=CC(C(F)F)=CC(Br)=N1)(=O)=O SNDGKBMVZALTTE-UHFFFAOYSA-N 0.000 description 2
- BNQORUWBURQFAX-UHFFFAOYSA-N 2-bromo-4-chloro-6-methylsulfonylpyridine Chemical compound CS(C1=CC(Cl)=CC(Br)=N1)(=O)=O BNQORUWBURQFAX-UHFFFAOYSA-N 0.000 description 2
- IAUMPEMWFBHRAG-UHFFFAOYSA-N 2-bromo-4-ethoxy-6-methylsulfonylpyridine Chemical compound CCOC1=CC(Br)=NC(S(C)(=O)=O)=C1 IAUMPEMWFBHRAG-UHFFFAOYSA-N 0.000 description 2
- DZOUUEGMVMYEEM-UHFFFAOYSA-N 2-bromo-4-methyl-6-methylsulfanylpyridine Chemical compound CSC1=CC(C)=CC(Br)=N1 DZOUUEGMVMYEEM-UHFFFAOYSA-N 0.000 description 2
- SSRDPRPPJXLYBV-UHFFFAOYSA-N 2-bromo-6-iodo-3,4-dimethoxypyridine Chemical compound COC1=CC(I)=NC(Br)=C1OC SSRDPRPPJXLYBV-UHFFFAOYSA-N 0.000 description 2
- JYEVBOIWTFEXGK-UHFFFAOYSA-N 2-bromo-6-iodo-3-propan-2-yloxypyridine Chemical compound CC(C)Oc1ccc(I)nc1Br JYEVBOIWTFEXGK-UHFFFAOYSA-N 0.000 description 2
- AANJGLLXOQVWES-UHFFFAOYSA-N 2-bromo-6-methylsulfanyl-3-propan-2-yloxypyridine Chemical compound CC(C)OC(C(Br)=N1)=CC=C1SC AANJGLLXOQVWES-UHFFFAOYSA-N 0.000 description 2
- PKOMXOAMEYEUQG-UHFFFAOYSA-N 2-bromo-6-methylsulfanyl-4-(oxan-4-yl)pyridine Chemical compound CSC1=CC(C2CCOCC2)=CC(Br)=N1 PKOMXOAMEYEUQG-UHFFFAOYSA-N 0.000 description 2
- SIDSDTKHWSPFJN-FIBGUPNXSA-N 2-bromo-6-methylsulfanyl-4-(trideuteriomethoxy)pyridine Chemical compound [2H]C([2H])([2H])OC1=CC(Br)=NC(SC)=C1 SIDSDTKHWSPFJN-FIBGUPNXSA-N 0.000 description 2
- HRYWGRKYHYENKV-UHFFFAOYSA-N 2-bromo-6-methylsulfanyl-4-phenoxypyridine Chemical compound CSC1=CC(OC2=CC=CC=C2)=CC(Br)=N1 HRYWGRKYHYENKV-UHFFFAOYSA-N 0.000 description 2
- SNIQAJRUBZUTRC-UHFFFAOYSA-N 2-bromo-6-methylsulfanylpyridin-4-amine Chemical compound CSC1=CC(N)=CC(Br)=N1 SNIQAJRUBZUTRC-UHFFFAOYSA-N 0.000 description 2
- UKLXSQIIBMMVIW-UHFFFAOYSA-N 2-bromo-6-methylsulfanylpyridine-4-carbonitrile Chemical compound CSC1=CC(C#N)=CC(Br)=N1 UKLXSQIIBMMVIW-UHFFFAOYSA-N 0.000 description 2
- MJSAHXZVWKAQLI-UHFFFAOYSA-N 2-bromo-6-methylsulfonyl-3-propan-2-yloxypyridine Chemical compound CC(C)OC(C(Br)=N1)=CC=C1S(C)(=O)=O MJSAHXZVWKAQLI-UHFFFAOYSA-N 0.000 description 2
- CONDQRNKNWLZQD-UHFFFAOYSA-N 2-bromo-6-methylsulfonyl-4-(oxetan-3-ylmethoxy)pyridine Chemical compound CS(C1=CC(OCC2COC2)=CC(Br)=N1)(=O)=O CONDQRNKNWLZQD-UHFFFAOYSA-N 0.000 description 2
- JNKHMFDILSGIQZ-UHFFFAOYSA-N 2-bromo-6-methylsulfonyl-4-phenoxypyridine Chemical compound CS(C1=CC(OC2=CC=CC=C2)=CC(Br)=N1)(=O)=O JNKHMFDILSGIQZ-UHFFFAOYSA-N 0.000 description 2
- QFPGUFUWKYKIFX-UHFFFAOYSA-N 2-bromo-6-methylsulfonyl-4-phenylpyridine Chemical compound CS(C1=CC(C2=CC=CC=C2)=CC(Br)=N1)(=O)=O QFPGUFUWKYKIFX-UHFFFAOYSA-N 0.000 description 2
- URCPVULNDTVIAP-UHFFFAOYSA-N 2-bromo-6-methylsulfonyl-4-propan-2-yloxypyridine Chemical compound CC(C)OC1=CC(Br)=NC(S(C)(=O)=O)=C1 URCPVULNDTVIAP-UHFFFAOYSA-N 0.000 description 2
- GONBBJCSTRMRRB-UHFFFAOYSA-N 2-bromo-6-methylsulfonylpyridin-4-amine Chemical compound CS(C1=CC(N)=CC(Br)=N1)(=O)=O GONBBJCSTRMRRB-UHFFFAOYSA-N 0.000 description 2
- DOSBGYNVIALPBI-UHFFFAOYSA-N 2-bromo-6-methylsulfonylpyridine Chemical compound CS(=O)(=O)C1=CC=CC(Br)=N1 DOSBGYNVIALPBI-UHFFFAOYSA-N 0.000 description 2
- PXZGEZKSYMZAGX-UHFFFAOYSA-N 2-bromo-6-methylsulfonylpyridine-4-carbonitrile Chemical compound CS(C1=CC(C#N)=CC(Br)=N1)(=O)=O PXZGEZKSYMZAGX-UHFFFAOYSA-N 0.000 description 2
- JBKINHFZTVLNEM-UHFFFAOYSA-N 2-bromoethoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCBr JBKINHFZTVLNEM-UHFFFAOYSA-N 0.000 description 2
- GOONRJUYQYHIEP-UHFFFAOYSA-N 2-chloro-4-(1-methoxyethyl)-6-methylsulfanylpyridine Chemical compound CC(C1=CC(Cl)=NC(SC)=C1)OC GOONRJUYQYHIEP-UHFFFAOYSA-N 0.000 description 2
- QYEMNWQCLAPMDK-UHFFFAOYSA-N 2-chloro-4-(1-methoxyethyl)-6-methylsulfonylpyridine Chemical compound CC(C1=CC(Cl)=NC(S(C)(=O)=O)=C1)OC QYEMNWQCLAPMDK-UHFFFAOYSA-N 0.000 description 2
- CDYHPDHSVZNJJH-UHFFFAOYSA-N 2-chloro-4-(3-methoxyazetidin-1-yl)-6-methylsulfanylpyridine Chemical compound COC(C1)CN1C1=CC(Cl)=NC(SC)=C1 CDYHPDHSVZNJJH-UHFFFAOYSA-N 0.000 description 2
- TZWCHJXKLNFSHW-UHFFFAOYSA-N 2-chloro-4-(3-methoxyazetidin-1-yl)-6-methylsulfonylpyridine Chemical compound COC(C1)CN1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 TZWCHJXKLNFSHW-UHFFFAOYSA-N 0.000 description 2
- JFBZLVJLBPYAGM-UHFFFAOYSA-N 2-chloro-4-(3-methoxycyclobutyl)-6-methylsulfanylpyridine Chemical compound COC(C1)CC1C1=CC(Cl)=NC(SC)=C1 JFBZLVJLBPYAGM-UHFFFAOYSA-N 0.000 description 2
- FBMVZCRVGCIOEG-UHFFFAOYSA-N 2-chloro-4-(4-methoxypiperidin-1-yl)-6-methylsulfanylpyridine Chemical compound COC(CC1)CCN1C1=CC(Cl)=NC(SC)=C1 FBMVZCRVGCIOEG-UHFFFAOYSA-N 0.000 description 2
- GTOQRHAUUBXIQA-UHFFFAOYSA-N 2-chloro-4-(4-methoxypiperidin-1-yl)-6-methylsulfonylpyridine Chemical compound COC(CC1)CCN1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 GTOQRHAUUBXIQA-UHFFFAOYSA-N 0.000 description 2
- ACCAYKUKQLMBLL-UHFFFAOYSA-N 2-chloro-6-methylsulfanyl-4-(trifluoromethyl)pyridine Chemical compound CSc1cc(cc(Cl)n1)C(F)(F)F ACCAYKUKQLMBLL-UHFFFAOYSA-N 0.000 description 2
- XEYZEWCZVUKDCZ-UHFFFAOYSA-N 2-chloro-6-methylsulfonyl-4-(trifluoromethyl)pyridine Chemical compound CS(C1=CC(C(F)(F)F)=CC(Cl)=N1)(=O)=O XEYZEWCZVUKDCZ-UHFFFAOYSA-N 0.000 description 2
- DPGSPRJLAZGUBQ-UHFFFAOYSA-N 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(C=C)OC1(C)C DPGSPRJLAZGUBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- MMCOQWZRPLXUAO-UHFFFAOYSA-N 3-bromo-5-methylsulfanylbenzonitrile Chemical compound CSc1cc(Br)cc(c1)C#N MMCOQWZRPLXUAO-UHFFFAOYSA-N 0.000 description 2
- MMJQJSQOTGZCHX-UHFFFAOYSA-N 3-hydroxycyclobutane-1-carbonitrile Chemical compound OC1CC(C#N)C1 MMJQJSQOTGZCHX-UHFFFAOYSA-N 0.000 description 2
- JWPBFHWOFVDCMO-UHFFFAOYSA-N 3-phenylmethoxycyclobutane-1-carbonitrile Chemical compound C1C(C#N)CC1OCC1=CC=CC=C1 JWPBFHWOFVDCMO-UHFFFAOYSA-N 0.000 description 2
- MBLWOPRZYVGFDF-UHFFFAOYSA-N 4-chloro-5-pyridazin-3-ylpyridin-2-amine Chemical compound NC1=NC=C(C2=CC=CN=N2)C(Cl)=C1 MBLWOPRZYVGFDF-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- GQJQOJQNLCYCMS-UHFFFAOYSA-N 6-bromo-2-fluoro-3-methylpyridine Chemical compound CC1=CC=C(Br)N=C1F GQJQOJQNLCYCMS-UHFFFAOYSA-N 0.000 description 2
- GOYFDRSWTGLHPS-UHFFFAOYSA-N 6-bromo-3-methoxy-2-methylsulfanylpyridine Chemical compound COC(C(SC)=N1)=CC=C1Br GOYFDRSWTGLHPS-UHFFFAOYSA-N 0.000 description 2
- LKDAXEZGQAVBOO-UHFFFAOYSA-N 6-bromo-3-methoxy-2-methylsulfonylpyridine Chemical compound COC(C(S(C)(=O)=O)=N1)=CC=C1Br LKDAXEZGQAVBOO-UHFFFAOYSA-N 0.000 description 2
- XRAYDESSNSYZNW-UHFFFAOYSA-N 6-bromo-3-methyl-2-methylsulfanylpyridine Chemical compound CC(C(SC)=N1)=CC=C1Br XRAYDESSNSYZNW-UHFFFAOYSA-N 0.000 description 2
- SWEIEMLGMWCZLW-UHFFFAOYSA-N 6-bromo-3-methyl-2-methylsulfonylpyridine Chemical compound CC(C(S(C)(=O)=O)=N1)=CC=C1Br SWEIEMLGMWCZLW-UHFFFAOYSA-N 0.000 description 2
- GZPJJPBNTXAUIB-UHFFFAOYSA-N 6-bromo-4-methylpyridine-2-sulfonyl chloride Chemical compound CC1=CC(Br)=NC(S(Cl)(=O)=O)=C1 GZPJJPBNTXAUIB-UHFFFAOYSA-N 0.000 description 2
- NYTYSLDZVTURTI-UHFFFAOYSA-N 7-bromo-2,3-dihydro-[1,4]dioxino[2,3-c]pyridine Chemical compound BrC1=NC=C2OCCOC2=C1 NYTYSLDZVTURTI-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- MTPSOHQPUVKYIE-UHFFFAOYSA-N BrC1=NC(=CC(=C1)OC1=CC=CC=C1)Br Chemical compound BrC1=NC(=CC(=C1)OC1=CC=CC=C1)Br MTPSOHQPUVKYIE-UHFFFAOYSA-N 0.000 description 2
- KPFULLQCBHASGQ-UHFFFAOYSA-N BrC1=NC(Br)=CC(C2=CCOCC2)=C1 Chemical compound BrC1=NC(Br)=CC(C2=CCOCC2)=C1 KPFULLQCBHASGQ-UHFFFAOYSA-N 0.000 description 2
- XRDIECYQZYSLFB-UHFFFAOYSA-N BrC1=NC(Br)=CC(C2CCOCC2)=C1 Chemical compound BrC1=NC(Br)=CC(C2CCOCC2)=C1 XRDIECYQZYSLFB-UHFFFAOYSA-N 0.000 description 2
- GKJDCHIIFQWYFB-UHFFFAOYSA-N CC(C)(C)[Si](C)(C)OCCOC1=CC(Br)=CC(Br)=C1 Chemical compound CC(C)(C)[Si](C)(C)OCCOC1=CC(Br)=CC(Br)=C1 GKJDCHIIFQWYFB-UHFFFAOYSA-N 0.000 description 2
- JZZZKJHRBZCBBN-UHFFFAOYSA-N CC(C)(C)[Si](C)(C)OCCOC1=CC(Br)=CC(S(C)(=O)=O)=C1 Chemical compound CC(C)(C)[Si](C)(C)OCCOC1=CC(Br)=CC(S(C)(=O)=O)=C1 JZZZKJHRBZCBBN-UHFFFAOYSA-N 0.000 description 2
- CGJSELDTKMQTQQ-UHFFFAOYSA-N CC(C)(C)[Si](C)(C)OCCOC1=CC(Br)=CC(SC)=C1 Chemical compound CC(C)(C)[Si](C)(C)OCCOC1=CC(Br)=CC(SC)=C1 CGJSELDTKMQTQQ-UHFFFAOYSA-N 0.000 description 2
- UMEFVPSVEXGHIL-UHFFFAOYSA-N CC(C)(C)[Si](C)(C)OCCOC1=CC(Br)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)(C)[Si](C)(C)OCCOC1=CC(Br)=NC(S(C)(=O)=O)=C1 UMEFVPSVEXGHIL-UHFFFAOYSA-N 0.000 description 2
- CXGGEXJJEVQCCA-UHFFFAOYSA-N CC(C1=CC(=NC(=C1)Cl)Cl)OC Chemical compound CC(C1=CC(=NC(=C1)Cl)Cl)OC CXGGEXJJEVQCCA-UHFFFAOYSA-N 0.000 description 2
- CYUXZHXEPCGWOB-UHFFFAOYSA-N CC(C1=CC(Br)=NC(Br)=C1)OC Chemical compound CC(C1=CC(Br)=NC(Br)=C1)OC CYUXZHXEPCGWOB-UHFFFAOYSA-N 0.000 description 2
- SFABNHDGMBNELE-UHFFFAOYSA-N CC(NC(C=C1N)=NC=C1C(N=N1)=CC=C1OC)=O Chemical compound CC(NC(C=C1N)=NC=C1C(N=N1)=CC=C1OC)=O SFABNHDGMBNELE-UHFFFAOYSA-N 0.000 description 2
- IHECXDKLPAPLPE-UHFFFAOYSA-N CC(NC1=NC=C(C2=CN(COCC[Si](C)(C)C)C=N2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CN(COCC[Si](C)(C)C)C=N2)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O IHECXDKLPAPLPE-UHFFFAOYSA-N 0.000 description 2
- ZXCMUCCWRVTZQL-UHFFFAOYSA-N CC(NC1=NC=C(C2=CN=CN2COCC[Si](C)(C)C)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O Chemical compound CC(NC1=NC=C(C2=CN=CN2COCC[Si](C)(C)C)C(NC2=NC(S(C)(=O)=O)=CC=C2)=C1)=O ZXCMUCCWRVTZQL-UHFFFAOYSA-N 0.000 description 2
- ZJHGQGAKDHMVTM-UHFFFAOYSA-N CC1(C)OC(COC2=CC(Br)=NC(S(C)(=O)=O)=C2)CO1 Chemical compound CC1(C)OC(COC2=CC(Br)=NC(S(C)(=O)=O)=C2)CO1 ZJHGQGAKDHMVTM-UHFFFAOYSA-N 0.000 description 2
- BEMXSULCCXLCPL-ZETCQYMHSA-N CC[C@H](C)OC1=CC(Br)=NC(S(C)(=O)=O)=C1 Chemical compound CC[C@H](C)OC1=CC(Br)=NC(S(C)(=O)=O)=C1 BEMXSULCCXLCPL-ZETCQYMHSA-N 0.000 description 2
- JCUIRMHJCMEKNQ-UHFFFAOYSA-N COC(C1)CC1C1=CC(Cl)=NC(Cl)=C1 Chemical compound COC(C1)CC1C1=CC(Cl)=NC(Cl)=C1 JCUIRMHJCMEKNQ-UHFFFAOYSA-N 0.000 description 2
- UJUVYXKNDMRNHK-UHFFFAOYSA-N COC(C1)CN1C1=CC(Cl)=NC(Cl)=C1 Chemical compound COC(C1)CN1C1=CC(Cl)=NC(Cl)=C1 UJUVYXKNDMRNHK-UHFFFAOYSA-N 0.000 description 2
- LNVKIAAXHLZEPR-UHFFFAOYSA-N COC(C=C(N=C1Br)SC)=C1OC Chemical compound COC(C=C(N=C1Br)SC)=C1OC LNVKIAAXHLZEPR-UHFFFAOYSA-N 0.000 description 2
- KPTPLKWXSXPBEE-UHFFFAOYSA-N COC(CC1)CCN1C1=CC(Cl)=NC(Cl)=C1 Chemical compound COC(CC1)CCN1C1=CC(Cl)=NC(Cl)=C1 KPTPLKWXSXPBEE-UHFFFAOYSA-N 0.000 description 2
- CRSOZVIRHQVWJW-UHFFFAOYSA-N COC1=CC=C(CC2(N)NC=C(C3OCCC3)C(NC3=CC(S(C)(=O)=O)=CC=C3)=C2)C=C1 Chemical compound COC1=CC=C(CC2(N)NC=C(C3OCCC3)C(NC3=CC(S(C)(=O)=O)=CC=C3)=C2)C=C1 CRSOZVIRHQVWJW-UHFFFAOYSA-N 0.000 description 2
- YAKWYQVVIBKKOB-UHFFFAOYSA-N COC1=CC=C(CNC2=NC=C(C3=CC=CO3)C(NC3=CC(S(C)(=O)=O)=CC=C3)=C2)C=C1 Chemical compound COC1=CC=C(CNC2=NC=C(C3=CC=CO3)C(NC3=CC(S(C)(=O)=O)=CC=C3)=C2)C=C1 YAKWYQVVIBKKOB-UHFFFAOYSA-N 0.000 description 2
- OOGCTIJJKJEKSX-XWEPSHTISA-N CO[C@H](C1)C[C@@H]1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 Chemical compound CO[C@H](C1)C[C@@H]1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 OOGCTIJJKJEKSX-XWEPSHTISA-N 0.000 description 2
- OOGCTIJJKJEKSX-OTSSQURYSA-N CO[C@H](C1)C[C@H]1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 Chemical compound CO[C@H](C1)C[C@H]1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 OOGCTIJJKJEKSX-OTSSQURYSA-N 0.000 description 2
- JCZPLNKBVGCNQJ-UHFFFAOYSA-N CS(=O)(=O)c1cc(Br)cc(c1)C#N Chemical compound CS(=O)(=O)c1cc(Br)cc(c1)C#N JCZPLNKBVGCNQJ-UHFFFAOYSA-N 0.000 description 2
- PPWZOISSGPMSPY-UHFFFAOYSA-N CS(C1=CC(OCC#N)=CC(Br)=N1)(=O)=O Chemical compound CS(C1=CC(OCC#N)=CC(Br)=N1)(=O)=O PPWZOISSGPMSPY-UHFFFAOYSA-N 0.000 description 2
- AOTKEAIREYRTLD-UHFFFAOYSA-N CS(C1=CC=CC(C(C2)(C(C3OCCC3)=CN=C2N)N)=C1)(=O)=O Chemical compound CS(C1=CC=CC(C(C2)(C(C3OCCC3)=CN=C2N)N)=C1)(=O)=O AOTKEAIREYRTLD-UHFFFAOYSA-N 0.000 description 2
- VOKLGUWYLQRPKC-UHFFFAOYSA-N CSC(N=C1Br)=CC2=C1OCCO2 Chemical compound CSC(N=C1Br)=CC2=C1OCCO2 VOKLGUWYLQRPKC-UHFFFAOYSA-N 0.000 description 2
- APNSGXOOHHKZNB-UHFFFAOYSA-N CSC1=CC(C2OCCOC2)=CC(Cl)=N1 Chemical compound CSC1=CC(C2OCCOC2)=CC(Cl)=N1 APNSGXOOHHKZNB-UHFFFAOYSA-N 0.000 description 2
- SOHNHMPRMJKRJT-ZETCQYMHSA-N C[C@@H](COCC1)N1C1=CC(Cl)=NC(Cl)=C1 Chemical compound C[C@@H](COCC1)N1C1=CC(Cl)=NC(Cl)=C1 SOHNHMPRMJKRJT-ZETCQYMHSA-N 0.000 description 2
- WDZINPRASPRKHR-QMMMGPOBSA-N C[C@@H](COCC1)N1C1=CC(Cl)=NC(SC)=C1 Chemical compound C[C@@H](COCC1)N1C1=CC(Cl)=NC(SC)=C1 WDZINPRASPRKHR-QMMMGPOBSA-N 0.000 description 2
- CEXGRHUELHPTNV-LLVKDONJSA-N C[C@H](COC1=CC(Br)=CC(Br)=C1)O[Si](C)(C)C(C)(C)C Chemical compound C[C@H](COC1=CC(Br)=CC(Br)=C1)O[Si](C)(C)C(C)(C)C CEXGRHUELHPTNV-LLVKDONJSA-N 0.000 description 2
- JTKWRYPCFPIPSY-GFCCVEGCSA-N C[C@H](COC1=CC(Br)=CC(SC)=C1)O[Si](C)(C)C(C)(C)C Chemical compound C[C@H](COC1=CC(Br)=CC(SC)=C1)O[Si](C)(C)C(C)(C)C JTKWRYPCFPIPSY-GFCCVEGCSA-N 0.000 description 2
- WDZINPRASPRKHR-MRVPVSSYSA-N C[C@H](COCC1)N1C1=CC(Cl)=NC(SC)=C1 Chemical compound C[C@H](COCC1)N1C1=CC(Cl)=NC(SC)=C1 WDZINPRASPRKHR-MRVPVSSYSA-N 0.000 description 2
- OSNBYDZEYDMTOM-UHFFFAOYSA-N C[Si](C)(C)CCOCN1C(C(C(NC2=NC(S(C)(=O)=O)=CC=C2)=C2)=CN=C2Cl)=CN=C1 Chemical compound C[Si](C)(C)CCOCN1C(C(C(NC2=NC(S(C)(=O)=O)=CC=C2)=C2)=CN=C2Cl)=CN=C1 OSNBYDZEYDMTOM-UHFFFAOYSA-N 0.000 description 2
- CCZZRMSMWWGOAG-UHFFFAOYSA-N C[Si](C)(C)CCOCN1C=NC(C(C(NC2=NC(S(C)(=O)=O)=CC=C2)=C2)=CN=C2Cl)=C1 Chemical compound C[Si](C)(C)CCOCN1C=NC(C(C(NC2=NC(S(C)(=O)=O)=CC=C2)=C2)=CN=C2Cl)=C1 CCZZRMSMWWGOAG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UWHPMSKBMVUBIE-UHFFFAOYSA-N ClC1=NC(Cl)=CC(C(C2)CC2OCC2=CC=CC=C2)=C1 Chemical compound ClC1=NC(Cl)=CC(C(C2)CC2OCC2=CC=CC=C2)=C1 UWHPMSKBMVUBIE-UHFFFAOYSA-N 0.000 description 2
- DBONLFULPBCAFB-UHFFFAOYSA-N ClC1=NC(Cl)=CC(C2OCCOC2)=C1 Chemical compound ClC1=NC(Cl)=CC(C2OCCOC2)=C1 DBONLFULPBCAFB-UHFFFAOYSA-N 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 description 2
- 102000008986 Janus Human genes 0.000 description 2
- 108050000950 Janus Proteins 0.000 description 2
- 229940122245 Janus kinase inhibitor Drugs 0.000 description 2
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- DKMIOYINYGJEQJ-UHFFFAOYSA-N NC(C=C(N=C1)Cl)=C1C(C=C1)=NC=C1F Chemical compound NC(C=C(N=C1)Cl)=C1C(C=C1)=NC=C1F DKMIOYINYGJEQJ-UHFFFAOYSA-N 0.000 description 2
- GUIKUWHXLJLIGZ-UHFFFAOYSA-N OC(C(C1)(CC1OCC1=CC=CC=C1)C1=CC(Cl)=NC(Cl)=C1)=O Chemical compound OC(C(C1)(CC1OCC1=CC=CC=C1)C1=CC(Cl)=NC(Cl)=C1)=O GUIKUWHXLJLIGZ-UHFFFAOYSA-N 0.000 description 2
- ADRKCVVZWWDPFX-UHFFFAOYSA-N OC(C1)CC1C1=CC(Cl)=NC(Cl)=C1 Chemical compound OC(C1)CC1C1=CC(Cl)=NC(Cl)=C1 ADRKCVVZWWDPFX-UHFFFAOYSA-N 0.000 description 2
- DAIKGGLMICNGJE-UHFFFAOYSA-N OCC(C1=CC(Cl)=NC(Cl)=C1)O Chemical compound OCC(C1=CC(Cl)=NC(Cl)=C1)O DAIKGGLMICNGJE-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 102000000887 Transcription factor STAT Human genes 0.000 description 2
- 108050007918 Transcription factor STAT Proteins 0.000 description 2
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- FBLLPCQLOGKHAL-FIBGUPNXSA-N [2H]C([2H])([2H])OC1=CC(Br)=NC(Br)=C1 Chemical compound [2H]C([2H])([2H])OC1=CC(Br)=NC(Br)=C1 FBLLPCQLOGKHAL-FIBGUPNXSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 239000013060 biological fluid Substances 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000000423 cell based assay Methods 0.000 description 2
- 238000004296 chiral HPLC Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 2
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 description 2
- 239000012053 oil suspension Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- SRKDUHUULIWXFT-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(C)(C)OC1 SRKDUHUULIWXFT-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-BYPYZUCNSA-N (2S)-butan-2-ol Chemical compound CC[C@H](C)O BTANRVKWQNVYAZ-BYPYZUCNSA-N 0.000 description 1
- PAORVUMOXXAMPL-SECBINFHSA-N (2s)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride Chemical compound CO[C@](C(Cl)=O)(C(F)(F)F)C1=CC=CC=C1 PAORVUMOXXAMPL-SECBINFHSA-N 0.000 description 1
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 description 1
- SFWWGMKXCYLZEG-RXMQYKEDSA-N (3r)-3-methylmorpholine Chemical compound C[C@@H]1COCCN1 SFWWGMKXCYLZEG-RXMQYKEDSA-N 0.000 description 1
- SFWWGMKXCYLZEG-YFKPBYRVSA-N (3s)-3-methylmorpholine Chemical compound C[C@H]1COCCN1 SFWWGMKXCYLZEG-YFKPBYRVSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 description 1
- UZHVXJZEHGSWQV-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole Chemical compound C1NCC2CCCC21 UZHVXJZEHGSWQV-UHFFFAOYSA-N 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- PWTFRUXTAFBWBW-UHFFFAOYSA-N 1,3-dibromo-5-(bromomethyl)benzene Chemical compound BrCC1=CC(Br)=CC(Br)=C1 PWTFRUXTAFBWBW-UHFFFAOYSA-N 0.000 description 1
- YBFLXHGNEOJUFQ-UHFFFAOYSA-N 1,3-dibromo-5-(difluoromethyl)benzene Chemical compound FC(F)C1=CC(Br)=CC(Br)=C1 YBFLXHGNEOJUFQ-UHFFFAOYSA-N 0.000 description 1
- UKHOUWWEEAOCTI-UHFFFAOYSA-N 1,3-dibromo-5-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC(Br)=CC(Br)=C1 UKHOUWWEEAOCTI-UHFFFAOYSA-N 0.000 description 1
- FNKCOUREFBNNHG-UHFFFAOYSA-N 1,3-dibromo-5-chlorobenzene Chemical compound ClC1=CC(Br)=CC(Br)=C1 FNKCOUREFBNNHG-UHFFFAOYSA-N 0.000 description 1
- OQZAQBGJENJMHT-UHFFFAOYSA-N 1,3-dibromo-5-methoxybenzene Chemical compound COC1=CC(Br)=CC(Br)=C1 OQZAQBGJENJMHT-UHFFFAOYSA-N 0.000 description 1
- DPKKOVGCHDUSAI-UHFFFAOYSA-N 1,3-dibromo-5-methylbenzene Chemical compound CC1=CC(Br)=CC(Br)=C1 DPKKOVGCHDUSAI-UHFFFAOYSA-N 0.000 description 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
- 125000005960 1,4-diazepanyl group Chemical group 0.000 description 1
- HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 description 1
- QRADKVYIJIAENZ-UHFFFAOYSA-N 1-[[bromo(difluoro)methyl]-ethoxyphosphoryl]oxyethane Chemical compound CCOP(=O)(C(F)(F)Br)OCC QRADKVYIJIAENZ-UHFFFAOYSA-N 0.000 description 1
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- JHLKSIOJYMGSMB-UHFFFAOYSA-N 1-bromo-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(Br)=C1 JHLKSIOJYMGSMB-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- FJNNGKMAGDPVIU-UHFFFAOYSA-N 2,4,6-trichloropyridine Chemical compound ClC1=CC(Cl)=NC(Cl)=C1 FJNNGKMAGDPVIU-UHFFFAOYSA-N 0.000 description 1
- IFFLKGMDBKQMAH-UHFFFAOYSA-N 2,4-diaminopyridine Chemical compound NC1=CC=NC(N)=C1 IFFLKGMDBKQMAH-UHFFFAOYSA-N 0.000 description 1
- ZDPXTYKMHYSMQW-UHFFFAOYSA-N 2,6-dibromo-4-chloropyridine Chemical compound ClC1=CC(Br)=NC(Br)=C1 ZDPXTYKMHYSMQW-UHFFFAOYSA-N 0.000 description 1
- XIPATZUHJFQGQC-UHFFFAOYSA-N 2,6-dibromo-4-nitropyridine Chemical compound [O-][N+](=O)C1=CC(Br)=NC(Br)=C1 XIPATZUHJFQGQC-UHFFFAOYSA-N 0.000 description 1
- NTFZVUOMTODHRO-UHFFFAOYSA-N 2,6-dibromopyridin-4-amine Chemical compound NC1=CC(Br)=NC(Br)=C1 NTFZVUOMTODHRO-UHFFFAOYSA-N 0.000 description 1
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 1
- SPDCLINNOKFXQL-UHFFFAOYSA-N 2,6-dibromopyridine-4-carbonitrile Chemical compound BrC1=CC(C#N)=CC(Br)=N1 SPDCLINNOKFXQL-UHFFFAOYSA-N 0.000 description 1
- KVNQWVYYVLCZKK-UHFFFAOYSA-N 2,6-dichloro-4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC(Cl)=NC(Cl)=C1 KVNQWVYYVLCZKK-UHFFFAOYSA-N 0.000 description 1
- MHXJETVNZPUVEN-UHFFFAOYSA-N 2-(2-chloroethoxy)acetic acid Chemical compound OC(=O)COCCCl MHXJETVNZPUVEN-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- DOSGEBYQRMBTGS-UHFFFAOYSA-N 2-(3,6-dihydro-2h-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CCOCC1 DOSGEBYQRMBTGS-UHFFFAOYSA-N 0.000 description 1
- BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 1
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
- JPQLYWPPNQEEQI-UHFFFAOYSA-N 2-bromo-4-cyclobutyloxy-6-methylsulfonylpyridine Chemical compound CS(C1=CC(OC2CCC2)=CC(Br)=N1)(=O)=O JPQLYWPPNQEEQI-UHFFFAOYSA-N 0.000 description 1
- FNIFJBSKGAQQFI-UHFFFAOYSA-N 2-bromo-4-cyclopentyloxy-6-methylsulfonylpyridine Chemical compound CS(C1=CC(OC2CCCC2)=CC(Br)=N1)(=O)=O FNIFJBSKGAQQFI-UHFFFAOYSA-N 0.000 description 1
- CRRMIKBAPPOPNW-UHFFFAOYSA-N 2-bromo-5-(bromomethyl)pyridine Chemical compound BrCC1=CC=C(Br)N=C1 CRRMIKBAPPOPNW-UHFFFAOYSA-N 0.000 description 1
- QQLWZJPMEHSISU-UHFFFAOYSA-N 2-bromo-5-fluoro-4-iodopyridine Chemical compound FC1=CN=C(Br)C=C1I QQLWZJPMEHSISU-UHFFFAOYSA-N 0.000 description 1
- UODINHBLNPPDPD-UHFFFAOYSA-N 2-bromo-5-fluoropyridine Chemical compound FC1=CC=C(Br)N=C1 UODINHBLNPPDPD-UHFFFAOYSA-N 0.000 description 1
- LLKRSJVPTKFSLS-UHFFFAOYSA-N 2-bromo-5-iodopyridine Chemical compound BrC1=CC=C(I)C=N1 LLKRSJVPTKFSLS-UHFFFAOYSA-N 0.000 description 1
- ZIDIKYIZXMYHAW-UHFFFAOYSA-N 2-bromo-6-fluoropyridine Chemical compound FC1=CC=CC(Br)=N1 ZIDIKYIZXMYHAW-UHFFFAOYSA-N 0.000 description 1
- KUFBWSKZJZIBFE-UHFFFAOYSA-N 2-bromo-6-methylsulfanyl-4-phenylpyridine Chemical compound C1=CC(C2=CC(SC)=NC(Br)=C2)=CC=C1 KUFBWSKZJZIBFE-UHFFFAOYSA-N 0.000 description 1
- RPPOATDSWDAKLR-UHFFFAOYSA-N 2-bromo-6-methylsulfonyl-4-(oxetan-3-yloxy)pyridine Chemical compound CS(C1=CC(OC2COC2)=CC(Br)=N1)(=O)=O RPPOATDSWDAKLR-UHFFFAOYSA-N 0.000 description 1
- IWMAIVUVFSURGJ-UHFFFAOYSA-N 2-bromo-6-methylsulfonyl-4-(oxolan-3-yloxy)pyridine Chemical compound CS(C1=CC(OC2COCC2)=CC(Br)=N1)(=O)=O IWMAIVUVFSURGJ-UHFFFAOYSA-N 0.000 description 1
- KCOGJPKDOPUIRR-UHFFFAOYSA-N 2-bromo-6-methylsulfonylpyrazine Chemical compound CS(C1=CN=CC(Br)=N1)(=O)=O KCOGJPKDOPUIRR-UHFFFAOYSA-N 0.000 description 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- OOGCTIJJKJEKSX-UHFFFAOYSA-N 2-chloro-4-(3-methoxycyclobutyl)-6-methylsulfonylpyridine Chemical compound COC(C1)CC1C1=CC(Cl)=NC(S(C)(=O)=O)=C1 OOGCTIJJKJEKSX-UHFFFAOYSA-N 0.000 description 1
- KANLPPVXESMXQH-UHFFFAOYSA-N 2-chloro-4-cyclopropyl-6-methylsulfonylpyridine Chemical compound CS(C1=CC(C2CC2)=CC(Cl)=N1)(=O)=O KANLPPVXESMXQH-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 description 1
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 1
- 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 1
- 125000004922 2-methyl-3-pentyl group Chemical group CC(C)C(CC)* 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- QUJGDNCWTBTBQD-UHFFFAOYSA-N 3,5-dibromobenzonitrile Chemical compound BrC1=CC(Br)=CC(C#N)=C1 QUJGDNCWTBTBQD-UHFFFAOYSA-N 0.000 description 1
- ILYSUJOMLYXAOC-UHFFFAOYSA-N 3-bromopyridazine Chemical compound BrC1=CC=CN=N1 ILYSUJOMLYXAOC-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- XDPCNPCKDGQBAN-UHFFFAOYSA-N 3-hydroxytetrahydrofuran Chemical compound OC1CCOC1 XDPCNPCKDGQBAN-UHFFFAOYSA-N 0.000 description 1
- AVPAYFOQPGPSCC-UHFFFAOYSA-N 3-methoxyazetidine Chemical compound COC1CNC1 AVPAYFOQPGPSCC-UHFFFAOYSA-N 0.000 description 1
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 1
- 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 1
- 125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 1
- MSAGLWTVMUDVDT-UHFFFAOYSA-N 3-oxocyclobutane-1-carbonitrile Chemical compound O=C1CC(C#N)C1 MSAGLWTVMUDVDT-UHFFFAOYSA-N 0.000 description 1
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ZEYSHALLPAKUHG-UHFFFAOYSA-N 4-methoxypiperidine Chemical compound COC1CCNCC1 ZEYSHALLPAKUHG-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- CXBLQEIODBBSQD-UHFFFAOYSA-N 4-methylpiperidin-4-ol Chemical compound CC1(O)CCNCC1 CXBLQEIODBBSQD-UHFFFAOYSA-N 0.000 description 1
- FBMGULVEPROMAT-UHFFFAOYSA-N 4-methylpyridine-2-sulfonamide Chemical compound CC1=CC=NC(S(N)(=O)=O)=C1 FBMGULVEPROMAT-UHFFFAOYSA-N 0.000 description 1
- 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
- HTMGQIXFZMZZKD-UHFFFAOYSA-N 5,6,7,8-tetrahydroisoquinoline Chemical compound N1=CC=C2CCCCC2=C1 HTMGQIXFZMZZKD-UHFFFAOYSA-N 0.000 description 1
- TYBBZOZWSLKHMV-UHFFFAOYSA-N 5-bromo-2-chloro-4-iodopyridine Chemical compound ClC1=CC(I)=C(Br)C=N1 TYBBZOZWSLKHMV-UHFFFAOYSA-N 0.000 description 1
- MGZWZNBANVSZLM-UHFFFAOYSA-N 5-bromo-2-chloropyridin-4-amine Chemical compound NC1=CC(Cl)=NC=C1Br MGZWZNBANVSZLM-UHFFFAOYSA-N 0.000 description 1
- DDOFUMWLNSICHU-UHFFFAOYSA-N 5-bromo-4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=C(Br)C=N1 DDOFUMWLNSICHU-UHFFFAOYSA-N 0.000 description 1
- BHCMXJKPZOPRNN-UHFFFAOYSA-N 5-iodo-1h-imidazole Chemical compound IC1=CN=CN1 BHCMXJKPZOPRNN-UHFFFAOYSA-N 0.000 description 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
- BZZKEPGENYLQSC-FIBGUPNXSA-N 6-(cyclopropanecarbonylamino)-4-[2-methoxy-3-(1-methyl-1,2,4-triazol-3-yl)anilino]-N-(trideuteriomethyl)pyridazine-3-carboxamide Chemical compound C1(CC1)C(=O)NC1=CC(=C(N=N1)C(=O)NC([2H])([2H])[2H])NC1=C(C(=CC=C1)C1=NN(C=N1)C)OC BZZKEPGENYLQSC-FIBGUPNXSA-N 0.000 description 1
- SJOBMIWECHDGAY-UHFFFAOYSA-N 6-bromo-2-fluoro-3-methoxypyridine Chemical compound COC1=CC=C(Br)N=C1F SJOBMIWECHDGAY-UHFFFAOYSA-N 0.000 description 1
- DBQUYESBMLNDPA-UHFFFAOYSA-N 6-bromo-4-methylpyridine-2-sulfonamide Chemical compound CC1=CC(S(N)(=O)=O)=NC(Br)=C1 DBQUYESBMLNDPA-UHFFFAOYSA-N 0.000 description 1
- XTHKRYHULUJQHN-UHFFFAOYSA-N 6-bromopyridin-3-amine Chemical compound NC1=CC=C(Br)N=C1 XTHKRYHULUJQHN-UHFFFAOYSA-N 0.000 description 1
- PTEFNEALEPSHLC-UHFFFAOYSA-N 6-bromopyridin-3-ol Chemical compound OC1=CC=C(Br)N=C1 PTEFNEALEPSHLC-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
- 229940124282 BMS-986165 Drugs 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 125000000172 C5-C10 aryl group Chemical group 0.000 description 1
- WNOFBQNPRYVZID-AULYBMBSSA-N CC(C)(C)[Si](C)(C)O[C@H](C1)C[C@@H]1OC1=CC(Br)=NC(S(C)(=O)=O)=C1 Chemical compound CC(C)(C)[Si](C)(C)O[C@H](C1)C[C@@H]1OC1=CC(Br)=NC(S(C)(=O)=O)=C1 WNOFBQNPRYVZID-AULYBMBSSA-N 0.000 description 1
- ILGIKHCMCDNBSK-KYZUINATSA-N CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](O)C1 Chemical compound CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](O)C1 ILGIKHCMCDNBSK-KYZUINATSA-N 0.000 description 1
- SWZWQOUKGBXTFU-UHFFFAOYSA-N CC(NC(N=C1)=CC(N)=C1C1=NC=C(C(F)(F)F)C=C1)=O Chemical compound CC(NC(N=C1)=CC(N)=C1C1=NC=C(C(F)(F)F)C=C1)=O SWZWQOUKGBXTFU-UHFFFAOYSA-N 0.000 description 1
- GDKKJHMDPZHEMH-UHFFFAOYSA-N COC1=CC=C(CNC(C2)=NC=C(C3OCCC3)C2(C2=CC(S(C)(=O)=O)=CC=C2)N)C=C1 Chemical compound COC1=CC=C(CNC(C2)=NC=C(C3OCCC3)C2(C2=CC(S(C)(=O)=O)=CC=C2)N)C=C1 GDKKJHMDPZHEMH-UHFFFAOYSA-N 0.000 description 1
- OKKGNJVBMPGNSH-UHFFFAOYSA-N COC1=CC=C(COC(C(Br)=N2)=CC=C2SC)C=C1 Chemical compound COC1=CC=C(COC(C(Br)=N2)=CC=C2SC)C=C1 OKKGNJVBMPGNSH-UHFFFAOYSA-N 0.000 description 1
- MVIBHOFWSRAPGB-UHFFFAOYSA-N CS(C1=CC=CC(NC(C=C(N)NC2)=C2C2OCCC2)=C1)(=O)=O Chemical compound CS(C1=CC=CC(NC(C=C(N)NC2)=C2C2OCCC2)=C1)(=O)=O MVIBHOFWSRAPGB-UHFFFAOYSA-N 0.000 description 1
- XTYLZLAVKNJSRO-DTORHVGOSA-N C[C@H](C1)O[C@@H](C)CN1C(C=N1)=CC=C1Br Chemical compound C[C@H](C1)O[C@@H](C)CN1C(C=N1)=CC=C1Br XTYLZLAVKNJSRO-DTORHVGOSA-N 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 208000032928 Dyslipidaemia Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 101000650817 Homo sapiens Semaphorin-4D Proteins 0.000 description 1
- 101000652482 Homo sapiens TBC1 domain family member 8 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000002227 Interferon Type I Human genes 0.000 description 1
- 108010014726 Interferon Type I Proteins 0.000 description 1
- 102000042838 JAK family Human genes 0.000 description 1
- 108091082332 JAK family Proteins 0.000 description 1
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000009328 Perro Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 102100027744 Semaphorin-4D Human genes 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 230000005867 T cell response Effects 0.000 description 1
- 102100030302 TBC1 domain family member 8 Human genes 0.000 description 1
- 102000015774 TYK2 Kinase Human genes 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- WXIONIWNXBAHRU-UHFFFAOYSA-N [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylidene]-dimethylazanium Chemical compound C1=CN=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 WXIONIWNXBAHRU-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000003281 allosteric effect Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 230000005784 autoimmunity Effects 0.000 description 1
- 125000004320 azepan-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 description 1
- 125000004267 aziridin-2-yl group Chemical group [H]N1C([H])([H])C1([H])* 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- GNTFBMAGLFYMMZ-UHFFFAOYSA-N bicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CCC2 GNTFBMAGLFYMMZ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000010256 biochemical assay Methods 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- KXVUSQIDCZRUKF-UHFFFAOYSA-N bromocyclobutane Chemical compound BrC1CCC1 KXVUSQIDCZRUKF-UHFFFAOYSA-N 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 102000003675 cytokine receptors Human genes 0.000 description 1
- 108010057085 cytokine receptors Proteins 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000005742 definitive hemopoiesis Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000005883 dithianyl group Chemical group 0.000 description 1
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 208000012997 experimental autoimmune encephalomyelitis Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 1
- 125000004281 furazan-3-yl group Chemical group [H]C1=NON=C1* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000011132 hemopoiesis Effects 0.000 description 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 102000047536 human TYK2 Human genes 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 1
- 125000004282 imidazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])N([H])C1([H])* 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 208000018615 immunodeficiency 35 Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229940043355 kinase inhibitor Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- MPOOBUXJJDKJOG-UHFFFAOYSA-M lithium;chloride;hydrochloride Chemical compound [Li+].Cl.[Cl-] MPOOBUXJJDKJOG-UHFFFAOYSA-M 0.000 description 1
- 238000003819 low-pressure liquid chromatography Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000010197 meta-analysis Methods 0.000 description 1
- XHXXWWGGXFUMAJ-UHFFFAOYSA-N methanethiol;sodium Chemical compound [Na].SC XHXXWWGGXFUMAJ-UHFFFAOYSA-N 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 208000004235 neutropenia Diseases 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000005061 octahydroisoindolyl group Chemical group C1(NCC2CCCCC12)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000003551 oxepanyl group Chemical group 0.000 description 1
- QMLWSAXEQSBAAQ-UHFFFAOYSA-N oxetan-3-ol Chemical compound OC1COC1 QMLWSAXEQSBAAQ-UHFFFAOYSA-N 0.000 description 1
- SWYHWLFHDVMLHO-UHFFFAOYSA-N oxetan-3-ylmethanol Chemical compound OCC1COC1 SWYHWLFHDVMLHO-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920003228 poly(4-vinyl pyridine) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004290 pyrazolidin-3-yl group Chemical group [H]N1N([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- MRTAVLDNYYEJHK-UHFFFAOYSA-M sodium;2-chloro-2,2-difluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)Cl MRTAVLDNYYEJHK-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001583 thiepanyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000005503 thioxanyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 230000010472 type I IFN response Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Definitions
- Disclosed herein is a compound of Formula (I) for inhibiting TYK2 and treating a disease associated with the undesirable tyk-2 activity (tyk-2 related diseases) , a method of using the compounds disclosed herein for treating inflammatory or autoimmune diseases, and a pharmaceutical composition comprising the same.
- Janus family of kinases includes JAK1, JAK2, JAK3, and tyrosine kinase 2 (Tyk2) and are nonreceptor tyrosine kinases that bind to the intracellular portion of cell surface cytokine receptors.
- the Janus kinases phosphorylate signal transducer and activator of transcription (STAT) proteins, which then dimerize, translocate to the nucleus, and activate gene transcription.
- STAT signal transducer and activator of transcription
- Tyrosine kinase 2 is a member of the Janus kinase (JAK) family of nonreceptor tyrosine kinases and has been shown to be critical in regulating the signal transduction cascade downstream of receptors for IL-12, IL-23 and type I interferons in both mice (Ishizaki, M. et al., “Involvement of Tyrosine Kinase-2 in Both the IL-12/TH1 and IL-23/TH17 Axes in vivo” , J. Immunol., 187: 181-189 (2011) ; Prchal-Murphyl, M.
- Tyk2 mediates the receptor-induced phosphorylation of members of the STAT family of transcription factors, an essential signal that leads to the dimerization of STAT proteins and the transcription of STAT-dependent pro-inflammatory genes.
- Tyk2-deficient mice are resistant to experimental model of colitis, psoriasis and multiple sclerosis, demonstrating the importance of Tyk2-mediated signaling in autoimmunity and related disorders (Ishizaki, M. et al., “Involvement of Tyrosine Kinase-2 in Both the IL-12/TH1 and IL-23/TH17 Axes in vivo” , J. Immunol., 187: 181-189 (2011) ; Oyamada, A. et al., “Tyrosine kinase 2 plays critical roles in the pathogenic CD4 T cell responses for the development of experimental autoimmune encephalomyelitis” , J. Immunol., 2009, 183, 7539-7546) .
- JAK inhibitors that have progressed into development are active site-directed inhibitors that bind to the adenosine triphosphate (ATP) site of the catalytic domain (also referred to as the JH1 or “Janus Homology 1” domain) of the JAK protein, which prevents catalytic activity of the kinase by blocking ATP, downstream phosphorylation, and resulting pathway signal transduction (Bryan, M. et al., “Kinase Inhibitors for the Treatment of Immunological Disorders: Recent Advances” , J. Med. Chem. 2018, 61, 9030-9058) .
- ATP adenosine triphosphate
- JAK2 is involved in hematopoiesis (Neubauer, H.; et al., “JAK2 deficiency defines an essential developmental checkpoint in definitive hematopoiesis” , Cell 1998, 93, 397-409) and the inhibition of JAK2 can cause side effects such as anemia, neutropenia, and increased infection risk and dyslipidemia (Wollenhaupt, J., et al., “Safety and efficacy of tofacitinib, an oral Janus Kinase Inhibitor, for the treatment of rheumatoid arthritis in open-label. J. Rheumatol.
- BMS986165 (WO2014074661A1, WO2018183649A1, WO2018183656A1 and WO2019232138A1) is a first-in-class of TYK2-JH2 inhibitor, currently undergoing multiple clinical trials in psoriasis, ulcerative colitis (UC) , lupus and systemic lupus erythematosus.
- TYK2-JH2 inhibitor which entered clinical trials is ABBV-712 (See, for example, WO2019178079A1, WO2019178079A9, JP6557436B1, and US2019276450A1) and it is in a clinical trial for psoriasis.
- JH2 pseudokinase domain of TYK2.
- JH2 pseudokinase
- JH2 pseudokinase domain of TYK2
- JAK3 JAK family members
- X is N or CH
- Y is N, NR 3 or CR 3 ;
- L 1 is a direct bond, - (CR a R b ) q -, -O-, -S-, -S (O) -, -SO 2 -, -C (O) -, C (O) O-, -OC (O) -, -NR a -, -O- (CR a R b ) q -, -S- (CR a R b ) q -, -S (O) - (CR a R b ) q -, -S (O) - (CR a R b ) q -, -SO 2 - (CR a R b ) q -, -C (O) - (CR a R b ) q -, C (O) O- (CR a R b ) q -, -OC (O) - (CR a R b ) q -, -NR a -
- R 1 is -C 1-6 alkyl, -haloC 1-6 alkyl, -C 1-6 alkoxy, -haloC 1-6 alkoxyl, -C 3-6 cycloalkyl, aryl, or -NR c R d ;
- each of -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, -C 3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl is independently and optionally substituted with at least one substituent selected from
- heterocyclyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , substituted or unsubstituted -C 1-6 alkyl, substituted or unsubstituted -C 1- 6 alkoxy or -C (O) NR m R; or,
- C 1-6 alkyl optionally substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 or C 1-6 alkoxy;
- R h is hydrogen, hydroxy, -NH 2 , -C 1-6 alkyl, C 1-6 alkyl substituted with hydroxy, or heterocyclyl
- R e , R f , and R g are each independently hydrogen, -C 1-6 alkyl, -C 1-6 alkoxy, -C 2-6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein each of -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally independently substituted with one to three substituents selected from cyano, -oxo-, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy, -C 3-6 cycloalkyl optionally substituted with
- R 5 is hydrogen or C 1-6 alkyl
- Cy 1 is 6-to 12-membered aryl or 5-to 14-membered heteroaryl, or 5-to 14-membered heterocyclyl, each of which is optionally substituted with at least one substituent R i ,
- each of -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, -C 3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with halogen, -OR m , -C (O) R m , -NR m R n , -C 1-6 alkyl, C 1-6 alkoxy-, C 1-6 alkyl substituted with -C 1-6 alkoxy or -oxo-;
- R j , R k , R l , R m , R n are each independently hydrogen, -C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl-, -C 2-6 alkenyl, -C 2- 6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
- fused ring system comprises 0-4 heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) and is optionally and independently substituted with halogen, -C 1- 6 alkyl, -C 1-6 alkoxy, C 1-6 alkyl substituted with halogen, C 1-6 alkoxy substituted with halogen or -C 3- 6 cycloalkyl;
- any of the said alkyl or alkoxy is optionally enriched in deuterium.
- X is N or CH
- L 1 is a direct bond, - (CR a R b ) q -, -O-, -S-, -S (O) -, -SO 2 -, -C (O) -, C (O) O-, -OC (O) -, -NR a -, -O- (CR a R b ) q -, -S- (CR a R b ) q -, -S (O) - (CR a R b ) q -, -S (O) - (CR a R b ) q -, -SO 2 - (CR a R b ) q -, -C (O) - (CR a R b ) q -, C (O) O- (CR a R b ) q -, -OC (O) - (CR a R b ) q -, -NR a -
- R a and R b are independently hydrogen, -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
- R 1 is -C 1-6 alkyl, -haloC 1-6 alkyl, -C 1-6 alkoxy, -haloC 1-6 alkoxyl, -C 3-6 cycloalkyl, aryl, or -NR m R n ;
- each of -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, -C 3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl is independently and optionally substituted with at least one substituents selected from cyano, oxo, halogen, C 1-6 alkyl optionally substituted with halogen, C 1-6 alkyl substituted with hydroxy (preferably, hydroxymethyl, hydroxyethyl) , -OR h , -C (O) NR m R n , -NH 2 , -C 1-6 alkyl substituted with -NH 2 or -C 1-6 alkyl substituted with -C 1-6 alkoxy -;
- R h is hydrogen, alkyl, hydroxy-C 1-6 alkyl or heterocyclyl
- R e , R f , and R g are each independently hydrogen, -C 1-6 alkyl, -C 1-6 alkoxy, -C 2-6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein each of -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally independently substituted with one to three substituents selected from halogen, hydroxy, cyano, or -C 1-6 alkoxy; -C 3-6 cycloalkyl optionally substituted with halogen, hydroxy, or C 1-6 alkoxy, or heterocyclyl;
- R 5 is hydrogen or C 1-6 alkyl
- Cy 1 is 6-to 12-membered aryl or 5-to 14-membered heteroaryl, or 5-to 14-membered heterocyclyl, each of which is optionally substituted with at least one substituent R i ,
- each of said -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, -C 3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with halogen, OR m , C (O) R m , -NR m R n , -C 1-6 alkyl, C 1-6 alkoxy-, C 1-6 alkoxy-C 1- 6 alkyl-, or oxo;
- R j , R k , R l , R m , R n are each independently hydrogen, -C 1-6 alkyl, -C 1-6 alkyl substituted with C 1-6 alkoxy, -C 2- 6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
- fused ring system comprises 0-4 heteroatoms selected from oxygen, nitrogen or sulfur as ring member (s) and is optionally and independently substituted with halogen, -C 1-6 alkyl, -C 1- 6 alkoxy, -haloC 1-6 alkyl, -haloC 1-6 alkoxy, or -C 3-6 cycloalkyl;
- any of the said alkyl or alkoxy is optionally enriched in deuterium.
- X is N and Y is CR 3 . In some embodiments, X is N and Y is N. In some embodiments, X is CH and Y is N.
- R 1 is -C 1-3 alkyl, -NR c R d or -C 3-6 cycloalkyl, preferably -NH 2 , methyl, ethyl, propyl, isopropyl, cyclopropyl or cyclopentyl.
- R 2 and R 4 are each independently hydrogen, halogen, -C 1-6 alkyl, or -C 1- 6 alkoxy, preferably hydrogen, fluoro, methyl, methoxy, ethoxy, or isopropoxy.
- R 3 is
- 3-to 6-membered heterocyclyl comprises one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (O) as ring member (s) , optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy; and
- R h is hydrogen, alkyl, or heterocyclyl
- - -C 3-6 cycloalkyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR m R n , hydroxy, -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1- 6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- heterocyclyl comprising one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , optionally substituted with at least one substituent independently selected from cyano, -oxo-, halogen, hydroxy, C 1-6 alkyl, alkoxy, -NRR m R n , or -C (O) NR m R n , and wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- R e is -C 1-6 alkyl, -C 3-6 cycloalkyl, 3-to 6-membered heterocyclyl , or aryl, wherein
- -C 1-6 alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR m R n , -C 1-6 alkoxy-, -C 3- 6 cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, C 1-6 alkoxy or -C (O) NR m R n , 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, C 1-6 alkyl or C 1-6 alkoxy; and,
- -C 3-6 cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , C 1-6 alkyl, C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1- 6 alkyl or C 1-6 alkoxy;
- - heteroaryl comprising one oxygen (O) , nitrogen (N) or sulfur (S) heteroatom as ring member, optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1- 6 alkoxy;
- R m and R n are independently selected from hydrogen or C 1-3 alkyl
- any of the said alkyl or alkoxy is optionally enriched in deuterium.
- R 3 is
- said 3-to 6-membered heterocyclyl comprises one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (O) as ring member (s) , optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1- 6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy, and,
- R h is hydrogen, alkyl or heterocyclyl (preferably 3-to 6-membered heterocyclyl, e.g., tetrahydrofuranyl, thiazolidinyl) ;
- - -C 3-6 cycloalkyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR m R n , hydroxy, -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1- 6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- heterocyclyl preferably 4-to 6-membered monocyclic saturated heterocyclyl, saturated mono-spiro heterocyclyl, saturated bicyclic fused heterocyclyl, or saturated bridged heterocyclyl, comprising one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , more preferably morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -C 1-6 alkyl, alkoxy, -NR m R n , or -C (O) NR m R n , and wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano,
- R e is -C 1-6 alkyl, -C 3-6 cycloalkyl, 3-to 6-membered heterocyclyl (preferably 4-to 6-membered monocyclic saturated heterocyclyl comprising one oxygen heteroatom as ring member) , or aryl, wherein
- -C 1-6 alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR m R n , -C 1-6 alkoxy-, -C 3- 6 cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, C 1-6 alkoxy or -C (O) NR m R n , 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, -C 1- 6 alkyl or -C 1-6 alkoxy; and,
- -C 3-6 cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, NR m R n , C 1-6 alkyl, C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1- 6 alkyl or C 1-6 alkoxy;
- - heteroaryl preferably 5-to 6-membered heteroaryl comprising one oxygen (O) , nitrogen (N) or sulfur (S) heteroatom as ring member, optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- R m and R n are independently selected from hydrogen or C 1-3 alkyl.
- R 3 is
- Said 3-to 6-membered heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl, thiazolidinyl or azetidinyl, each of which is optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , C 1- 6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy, and, R h is hydrogen, C 1-6 alkyl or 3-to 6-membered heterocyclyl (e.g., tetrahydro
- - -C 3-6 cycloalkyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, NR m R n , hydroxy, -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , hydroxy, or C 1-6 alkoxy, wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- - heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, C 1-6 alkyl, alkoxy, -NRR m R n , or -C (O) NR m R n , and wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or -C 1-6 alkoxy;
- R e is -C 1-6 alkyl, -C 3-6 cycloalkyl, 4-to 6-membered monocyclic saturated heterocyclyl comprising one oxygen heteroatom as ring member, or C 6-10 aryl, wherein
- -C 1-6 alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR m R n , -C 1-6 alkoxy-, -C 3- 6 cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, -C 1- 6 alkyl or -C 1-6 alkoxy; and,
- -C 3-6 cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, NR m R n , C 1-6 alkyl, C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1- 6 alkyl or C 1-6 alkoxy;
- - 5-to 6-membered heteroaryl selected from pyridinyl, pyridazinyl, pyrazinyl, thiazolyl or isoxazolyl, each of which is optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- R m and R n are independently selected from hydrogen or -C 1-3 alkyl.
- R 3 is
- - -C 1-4 alkyl optionally substituted with at least one substituent independently selected from halogen, hydroxy, C 1-3 alkoxy, thiazolidin-3-yl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , or -C 1-3 alkyl;
- - -C 3-6 cycloalkyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR m R n , hydroxy, -C 1-6 alkyl, or -C 1-6 alkoxy, wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1- 6 alkyl or -C 1-3 alkoxy;
- - heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, C 1-6 alkyl, alkoxy, -NR m R n , or -C (O) NR m R n , and wherein -C 1- 6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or -C 1-6 alkoxy;
- R e is -C 1-6 alkyl, -C 3-6 cycloalkyl, 4-to 6-membered monocyclic saturated heterocyclyl comprising one oxygen heteroatom as ring member, or C 6-10 aryl, wherein
- -C 1-6 alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR m R n , -C 1-6 alkoxy-, -C 3- 6 cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or - C (O) NR m R n , 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, -C 1- 6 alkyl or -C 1-6 alkoxy; and,
- -C 3-6 cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1- 6 alkyl or -C 1-6 alkoxy;
- - 5-to 6-membered heteroaryl selected from pyridinyl, pyridazinyl, pyrazinyl, thiazolyl or isoxazolyl, each of which is optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or -C 1-6 alkoxy;
- R m and R n are independently selected from hydrogen or -C 1-3 alkyl.
- R 3 is
- - cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl each of which is optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR m R n , hydroxy, -C 1-3 alkyl, or -C 1-3 alkoxy, wherein -C 1-3 alkyl or C 1-3 alkoxy is optionally substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-3 alkyl or -C 1-3 alkoxy;
- heterocyclyl is selected from morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, pyrrolidine-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1, 4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, azetidin-1-yl, azetidine-2-yl, azetidin-3-yl, 5-azaspiro [2.4] heptanyl, 3-azabicyclo [3.1.0] hexan-3-yl or 2-azabicyclo [3.1.0] hexan-2-yl, each of
- - 5-to 6-membered heteroaryl selected from pyridin-1-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-1-yl, pyridazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-1-yl, pyrazin-2-yl, thiazol-2-yl, thiazol-3-yl, thiazol-4-yl, isoxazol-2-yl, isoxazol-3-yl or isoxazol-4-yl, each of which is optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-3 alkyl, -C 1-3 alkoxy or -C (O) NR m R n , wherein -C 1-3 alkyl
- R 3 is
- (R 1 and R 2 ) , or (R 2 and R 3 ) , or (R 3 and R 4 ) together with the atoms to which they are attached, form a fused 5-to 7-membered ring system, said fused ring system comprises 0-2 oxygen heteroatoms as ring member (s) and is optionally and independently substituted with halogen, -C 1- 6 alkyl, -C 1-6 alkoxy, -haloC 1-6 alkyl, -haloC 1-6 alkoxy, or -C 3-6 cycloalkyl.
- R 1 and R 2 together with the atoms to which they are attached, form a fused ring system selected from or R 2 and R 3 , together with the atoms to which they are attached, form a fused ring system R 3 and R 4 , together with the atoms to which they are attached, form a fused ring system selected from and wherein each of fused ring system is optionally and independently substituted with halogen, -C 1-6 alkyl, -C 1-6 alkoxy, -haloC 1-6 alkyl, -haloC 1-6 alkoxy, or -C 3-6 cycloalkyl .
- Cy 1 is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
- Cy 1 is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
- said 5-to 7-membered monocyclic heteroaryl comprising 1, 2, 3 or 4 heteroatom (s) selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , preferably pyrazolyl, triazolyl, imidazolyl, thiazolyl, oxazolyl, furanyl, pyridinyl, pyridazinyl, pyrazinyl or pyrimidinyl, said monocyclic heteroaryl is optionally substituted with one or two substituents selected from
- -C 1-6 alkyl optionally substituted with halogen, hydroxy, -C 1-6 alkoxy, -C (O) R m (preferably R m is morpholinyl) , or -NR m R n ;
- heterocyclyl optionally substituted with halogen, C 1-6 alkyl-, -C 1-6 alkyl substituted with -C 1-6 alkoxy, or oxo; preferably said heterocyclyl is selected from tetrahydrofuranyl (preferably tetrahydrofuran-3-yl) , morpholinyl (preferably morpholino) , 2-oxa-5-azabicyclo [2.2.1] heptanyl (preferably 2-oxa-5-azabicyclo [2.2.1] heptan-2-yl) , 8-oxa-3-azabicyclo [3.2.1] octanyl (preferably 8-oxa-3-azabicyclo [3.2.1] octan-8-yl) , isoindolinyl (preferably isoindolin-2-yl) , each of which is optionally substituted with methyl, ethyl, propyl, isopropyl, isobutyl, tert
- v. -C 3-6 cycloalkyl optionally substituted with halogen, -oxo, -C 1-6 alkyl, C 1-6 alkoxy-, or -C 1-6 alkyl substituted with -C 1-6 alkoxy; or
- R j is -C 1-6 alkyl, -C 1-6 alkyl substituted with -C 1-6 alkoxy, or heterocyclyl;
- said 7-to 14-membered bicyclic or tricyclic heteroaryl comprising 1, 2, or 3 heteroatom (s) as ring member (s) , preferably benzoimidazolyl, imidazopyrimidinyl, pyrazolopyrazinyl, pyrazolopyrimidinyl, benzothiophenyl, benzothiazolyl, benzoisoxazolyl, benzooxazolyl, benzoisothiazolyl, imidazopyridazinyl, imidazopyridazinyl; dihydro-4H-furo [3, 2-c] pyranyl, 6, 7-dihydro-4H-thieno [3, 2-c] pyranyl, 2, 3-dihydropyrazolo [5, 1-b] oxazolyl, 4, 5, 6, 7-tetrahydrofuro [3, 2-c] pyridinyl, 1, 3a, 4, 6, 7, 7a- hexahydropyrano [4, 3-c]
- Cy 1 is a 7-to 14-membered bicyclic heteroaryl which is a pyridinyl, pyrazolyl, thienyl, or thiazolyl ring fused with a 5-or 6-membered heterocyclyl ring, wherein said 5-or 6-membered heterocyclyl ring comprising one or two heteroatoms selected from oxygen or nitrogen as ring member (s) and said 5-or 6-membered heterocyclyl ring is optionally substituted with one or two C 1-6 alkyl or oxo, preferably two C 1-6 alkyl, more preferably two methyl, most preferably two methyl on the same carbon atom.
- Cy 1 is a 7-to 14-membered bicyclic heteroaryl which is a pyridinyl ring fused with a 5-or 6-membered heterocyclyl ring, wherein said 5-or 6-membered heterocyclyl ring comprising one or two heteroatoms selected from oxygen (O) or nitrogen (N) as ring member (s) and said 5-or 6-membered heterocyclyl ring is optionally substituted with one or two C 1-6 alkyl or oxo, preferably two C 1-6 alkyl, more preferably two methyl, most preferably two methyl on the same carbon atom.
- Cy 1 is a 7-to 14-membered bicyclic heteroaryl which is a pyridinyl ring fused with a 5-or 6-membered heterocyclyl ring, wherein said 5-or 6-membered heterocyclyl ring comprising two oxygen atoms as ring member (s) and said 5-or 6-membered heterocyclyl ring is optionally substituted with one or two C 1-6 alkyl, preferably two C 1-6 alkyl, more preferably two methyl, most preferably two methyl on the same carbon atom.
- Cy 1 is a 7-to 14-membered bicyclic heteroaryl which is a pyridinyl ring fused with 1, 4-dioxane ring, wherein said 1, 4-dioxane ring is optionally substituted with one or two C 1-6 alkyl, preferably two C 1-6 alkyl, more preferably two methyl, most preferably two methyl on the same carbon atom; any of the said alkyl or alkoxy is optionally enriched in deuterium.
- Cy 1 is preferably
- Cy 1 is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
- X is N or CH
- L 1 is a direct bond, - (CR a R b ) q -, -O-, -S-, -S (O) -, -SO 2 -, -C (O) -, C (O) O-, -OC (O) -, -NR a -, -O- (CR a R b ) q -, -S- (CR a R b ) q -, -S (O) - (CR a R b ) q -, -S (O) - (CR a R b ) q -, -SO 2 - (CR a R b ) q -, -C (O) - (CR a R b ) q -, C (O) O- (CR a R b ) q -, -OC (O) - (CR a R b ) q -, -NR a -
- R a and R b are independently hydrogen, -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
- each of -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, -C 3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl is independently and optionally substituted with at least one substituents selected from halogen, hydroxy-C 1- 6 alkyl (preferably, hydroxymethyl) , -OR h , or C 1-6 alkoxy-C 1-6 alkyl-;
- R h is hydrogen, alkyl, or heterocyclyl
- R e , R f , and R g are each independently hydrogen, -C 1-6 alkyl, -C 1-6 alkoxy, -C 2-6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein each of -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally independently substituted with one to three substituents selected from halogen, hydroxy, cyano, -C 1-6 alkoxy; -C 3-6 cycloalkyl optionally substituted with halogen, hydroxy, or C 1-6 alkoxy;
- R 5 is hydrogen or C 1-6 alkyl
- Cy 1 is 6-to 12-membered aryl or 5-to 14-membered heteroaryl, or 5-to 14-membered heterocyclyl, each of which is optionally substituted with at least one substituent R i ,
- each of said -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, -C 3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with halogen, OR m , C (O) R m , -NR m R n , -C 1-6 alkyl, C 1-6 alkoxy-, C 1-6 alkoxy-C 1- 6 alkyl-, or oxo;
- R j , R k , R l , R m , R n are each independently hydrogen, -C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl-, -C 2-6 alkenyl, -C 2- 6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
- fused ring system comprises 0-4 heteroatoms selected from oxygen, nitrogen or sulfur as ring member (s) and is optionally and independently substituted with halogen, -C 1-6 alkyl, -C 1- 6 alkoxy, -haloC 1-6 alkyl, -haloC 1-6 alkoxy, or -C 3-6 cycloalkyl;
- any of the said alkyl or alkoxy can be optionally enriched in deuterium.
- X is N or CH
- L 1 is a direct bond
- R 1 is -C 1-6 alkyl, or -haloC 1-6 alkyl
- each of R 2 and R 4 is independently hydrogen, halogen, -C 1-6 alkyl or -C 1-6 alkoxy;
- each of -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, -C 3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl is independently and optionally substituted with at least one substituents selected from
- heterocyclyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , substituted or unsubstituted -C 1-6 alkyl, substituted or unsubstituted -C 1- 6 alkoxy or -C (O) NR m R; or,
- C 1-6 alkyl optionally substituted with halogen, -C 1-6 alkyl substituted with hydroxy (preferably, hydroxymethyl, hydroxyethyl) , -C 1-6 alkyl substituted with -NH 2 , -NH 2 or -C 1-6 alkyl substituted with C 1- 6 alkoxy;
- R h is hydrogen, hydroxy, alkyl, substituted with hydroxy, or heterocyclyl
- R e , R f , and R g are each independently hydrogen, -C 1-6 alkyl, -C 1-6 alkoxy, -C 2-6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein each of -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally independently substituted with one to three substituents selected from halogen, hydroxy, cyano, -oxo-, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy; -C 3-6 cycloalkyl optionally substituted with halogen, hydroxy, or C 1-6 alkoxy, -C (O) NR m R n , or heterocyclyl;
- R 5 is hydrogen or C 1-6 alkyl
- Cy 1 is a 7-to 14-membered bicyclic or tricyclic heterocyclyl or heteroaryl having 1, 2, or 3 heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , which is optionally substituted with at least one substituent R i ,
- each of said -C 1-6 alkyl, -C 2-6 alkenyl, -C 2-6 alkynyl, -C 3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with halogen, OR m , C (O) R m , -NR m R n , -C 1-6 alkyl, C 1-6 alkoxy-, C 1-6 alkyl substituted with -C 1-6 alkoxy, or oxo;
- R j , R k , R l , R m , R n are each independently hydrogen, -C 1-6 alkyl, -C 1-6 alkyl substituted with C 1-6 alkoxy, -C 2- 6 alkenyl, -C 2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
- fused ring system comprises 0-4 heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) and is optionally and independently substituted with halogen, -C 1- 6 alkyl, -C 1-6 alkoxy, -haloC 1-6 alkyl, -haloC 1-6 alkoxy, or -C 3-6 cycloalkyl;
- any of the said alkyl or alkoxy is optionally enriched in deuterium.
- R 1 is -C 1-3 alkyl, preferably methyl, ethyl, propyl, or isopropyl.
- R 2 and R 4 are each independently hydrogen, halogen, -C 1-3 alkyl, or -C 1- 3 alkoxy, preferably hydrogen, fluoro, methyl, methoxy, ethoxy, or isopropoxy.
- R 3 is
- 3-to 6-membered heterocyclyl comprises one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (O) as ring member (s) , optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy; and
- R h is hydrogen, alkyl, or heterocyclyl
- - -C 3-6 cycloalkyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR m R n , hydroxy, -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1- 6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- heterocyclyl comprising one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , optionally substituted with at least one substituent independently selected from cyano, -oxo-, halogen, hydroxy, C 1-6 alkyl, alkoxy, -NRR m R n , or -C (O) NR m R n , and wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- R e is -C 1-6 alkyl, -C 3-6 cycloalkyl, 3-to 6-membered heterocyclyl , or aryl, wherein
- -C 1-6 alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR m R n , -C 1-6 alkoxy-, -C 3- 6 cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, C 1-6 alkoxy or -C (O) NR m R n , 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, C 1-6 alkyl or C 1-6 alkoxy; and,
- -C 3-6 cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , C 1-6 alkyl, C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1- 6 alkyl or C 1-6 alkoxy;
- - heteroaryl comprising one oxygen (O) , nitrogen (N) or sulfur (S) heteroatom as ring member, optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1- 6 alkoxy;
- R m and R n are independently selected from hydrogen or C 1-3 alkyl
- any of the said alkyl or alkoxy is optionally enriched in deuterium.
- R 3 is heterocyclyl comprising one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , optionally substituted with at least one substituent independently selected from cyano, -oxo-, halogen, hydroxy, C 1-6 alkyl, alkoxy, -NRR m R n , or -C (O) NR m R n , and wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy.
- R 3 is
- Said 3-to 6-membered heterocyclyl comprises one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (O) as ring member (s) , optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1- 6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy, and,
- R h is hydrogen, alkyl or heterocyclyl (preferably 3-to 6-membered heterocyclyl, e.g., tetrahydrofuranyl, thiazolidinyl) ;
- - -C 3-6 cycloalkyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR m R n , hydroxy, -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1- 6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- heterocyclyl preferably 4-to 6-membered monocyclic saturated heterocyclyl, saturated mono-spiro heterocyclyl, saturated bicyclic fused heterocyclyl, or saturated bridged heterocyclyl, comprising one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , more preferably morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -C 1-6 alkyl, alkoxy, -NR m R n , or -C (O) NR m R n , and wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano,
- R e is -C 1-6 alkyl, -C 3-6 cycloalkyl, 3-to 6-membered heterocyclyl (preferably 4-to 6-membered monocyclic saturated heterocyclyl comprising one oxygen heteroatom as ring member) , or aryl, wherein
- -C 1-6 alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR m R n , -C 1-6 alkoxy-, -C 3- 6 cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, C 1-6 alkoxy or -C (O) NR m R n , 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, -C 1- 6 alkyl or -C 1-6 alkoxy; and,
- -C 3-6 cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, NR m R n , C 1-6 alkyl, C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1- 6 alkyl or C 1-6 alkoxy;
- - heteroaryl preferably 5-to 6-membered heteroaryl comprising one oxygen (O) , nitrogen (N) or sulfur (S) heteroatom as ring member, optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- R m and R n are independently selected from hydrogen or C 1-3 alkyl.
- R 3 is heterocyclyl, preferably 4-to 6-membered monocyclic saturated heterocyclyl, saturated mono-spiro heterocyclyl, saturated bicyclic fused heterocyclyl, or saturated bridged heterocyclyl, comprising one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , more preferably morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -C 1-6 alkyl, alkoxy, -NR m R n , or -C (O) NR m R n , and wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently
- R 3 is
- Said 3-to 6-membered heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl, thiazolidinyl or azetidinyl, each of which is optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , C 1- 6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy, and, R h is hydrogen, C 1-6 alkyl or 3-to 6-membered heterocyclyl (e.g., tetrahydro
- - -C 3-6 cycloalkyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, NR m R n , hydroxy, -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , hydroxy, or C 1-6 alkoxy, wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- - heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, C 1-6 alkyl, alkoxy, -NRR m R n , or -C (O) NR m R n , and wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or -C 1-6 alkoxy;
- R e is -C 1-6 alkyl, -C 3-6 cycloalkyl, 4-to 6-membered monocyclic saturated heterocyclyl comprising one oxygen heteroatom as ring member, or C 6-10 aryl, wherein
- -C 1-6 alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR m R n , -C 1-6 alkoxy-, -C 3- 6 cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, -C 1- 6 alkyl or -C 1-6 alkoxy; and,
- -C 3-6 cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, NR m R n , C 1-6 alkyl, C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1- 6 alkyl or C 1-6 alkoxy;
- - 5-to 6-membered heteroaryl selected from pyridinyl, pyridazinyl, pyrazinyl, thiazolyl or isoxazolyl, each of which is optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or C 1-6 alkoxy;
- R m and R n are independently selected from hydrogen or -C 1-3 alkyl.
- R 3 is heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, C 1-6 alkyl, alkoxy, -NRR m R n , or -C (O) NR m R n , and wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or -C 1-6 alkoxy.
- R 3 is
- - -C 1-4 alkyl optionally substituted with at least one substituent independently selected from halogen, hydroxy, C 1-3 alkoxy, thiazolidin-3-yl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , or -C 1-3 alkyl;
- - -C 3-6 cycloalkyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR m R n , hydroxy, -C 1-6 alkyl, or -C 1-6 alkoxy, wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1- 6 alkyl or -C 1-3 alkoxy;
- - heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, C 1-6 alkyl, alkoxy, -NR m R n , or -C (O) NR m R n , and wherein -C 1- 6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or -C 1-6 alkoxy;
- R e is -C 1-6 alkyl, -C 3-6 cycloalkyl, 4-to 6-membered monocyclic saturated heterocyclyl comprising one oxygen heteroatom as ring member, or C 6-10 aryl, wherein
- -C 1-6 alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR m R n , -C 1-6 alkoxy-, -C 3- 6 cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, -C 1- 6 alkyl or -C 1-6 alkoxy; and,
- -C 3-6 cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1- 6 alkyl or -C 1-6 alkoxy;
- - 5-to 6-membered heteroaryl selected from pyridinyl, pyridazinyl, pyrazinyl, thiazolyl or isoxazolyl, each of which is optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-6 alkyl, -C 1-6 alkoxy or -C (O) NR m R n , wherein -C 1-6 alkyl or -C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or -C 1-6 alkoxy;
- R m and R n are independently selected from hydrogen or -C 1-3 alkyl.
- R 3 is heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, C 1-6 alkyl, alkoxy, -NR m R n , or -C (O) NR m R n , and wherein -C 1-6 alkyl or C 1-6 alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-6 alkyl or -C 1-6 alkoxy
- R 3 is
- - cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl each of which is optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR m R n , hydroxy, -C 1-3 alkyl, or -C 1-3 alkoxy, wherein -C 1-3 alkyl or C 1-3 alkoxy is optionally substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2 , -C 1-3 alkyl or -C 1-3 alkoxy;
- heterocyclyl is selected from morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, pyrrolidine-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1, 4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, azetidin-1-yl, azetidine-2-yl, azetidin-3-yl, 5-azaspiro [2.4] heptanyl, 3-azabicyclo [3.1.0] hexan-3-yl or 2-azabicyclo [3.1.0] hexan-2-yl, each of
- - 5-to 6-membered heteroaryl selected from pyridin-1-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-1-yl, pyridazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-1-yl, pyrazin-2-yl, thiazol-2-yl, thiazol-3-yl, thiazol-4-yl, isoxazol-2-yl, isoxazol-3-yl or isoxazol-4-yl, each of which is optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR m R n , -C 1-3 alkyl, -C 1-3 alkoxy or -C (O) NR m R n , wherein -C 1-3 alkyl
- R 3 is heterocyclyl is selected from morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, pyrrolidine-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1, 4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, azetidin-1-yl, azetidine-2-yl, azetidin-3-yl, 5- azaspiro [2.4] heptanyl, 3-azabicyclo [3.1.0] hexan-3-yl or 2-azabicyclo [3.1.0] hex
- R 3 is
- R 3 is
- R 3 is morpholino, 3-methyl-morpholino, 3 (R) -methyl-morpholino, or 3 (S) -methyl-morpholino.
- (R 1 and R 2 ) , or (R 2 and R 3 ) , or (R 3 and R 4 ) together with the atoms to which they are attached, form a fused 5-to 7-membered ring system, said fused ring system comprises 0-2 oxygen heteroatoms as ring member (s) and is optionally and independently substituted with halogen, -C 1- 6 alkyl, -C 1-6 alkoxy, -haloC 1-6 alkyl, -haloC 1-6 alkoxy, or -C 3-6 cycloalkyl.
- R 1 and R 2 together with the atoms to which they are attached, form a fused ring system selected from or R 2 and R 3 , together with the atoms to which they are attached, form a fused ring system R 3 and R 4 , together with the atoms to which they are attached, form a fused ring system selected from and wherein each of fused ring system is optionally and independently substituted with halogen, -C 1-6 alkyl, -C 1-6 alkoxy, -haloC 1-6 alkyl, -haloC 1-6 alkoxy, or -C 3-6 cycloalkyl .
- Cy 1 is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
- said 7-to 14-membered bicyclic or tricyclic heteroaryl comprising 1, 2, or 3 heteroatom (s) selected from oxygen, nitrogen or sulfur as ring member (s) , preferably benzoimidazolyl, imidazopyrimidinyl, pyrazolopyrazinyl, pyrazolopyrimidinyl, benzothiophenyl, benzothiazolyl, benzoisoxazolyl, benzooxazolyl, benzoisothiazolyl, imidazopyridazinyl, imidazopyridazinyl; dihydro-4H-furo [3, 2- c] pyranyl, 6, 7-dihydro-4H-thieno [3, 2-c] pyranyl, 2, 3-dihydropyrazolo [5, 1-b] oxazolyl, 4, 5, 6, 7-tetrahydrofuro [3, 2-c] pyridinyl, 1, 3a, 4, 6, 7, 7a-hexahydropyr
- Cy 1 is a 7-to 14-membered bicyclic heteroaryl which is a pyridinyl, pyrazolyl, thienyl, or thiazolyl ring fused with a 5-or 6-membered heterocyclyl ring, wherein said 5-or 6-membered heterocyclyl ring comprising one or two heteroatoms selected from oxygen or nitrogen as ring member (s) and said 5-or 6-membered heterocyclyl ring is optionally substituted with one or two C 1-6 alkyl or oxo, preferably two C 1-6 alkyl, more preferably two methyl, most preferably two methyl on the same carbon atom.
- Cy 1 is a 7-to 14-membered bicyclic heteroaryl which is a pyridinyl ring fused with a 5-or 6-membered heterocyclyl ring, wherein said 5-or 6-membered heterocyclyl ring comprising one or two heteroatoms selected from oxygen or nitrogen as ring member (s) and said 5-or 6-membered heterocyclyl ring is optionally substituted with one or two C 1-6 alkyl or oxo, preferably two C 1- 6 alkyl, more preferably two methyl, most preferably two methyl on the same carbon atom.
- Cy 1 is a 7-to 14-membered bicyclic heteroaryl which is a pyridinyl ring fused with a 5-or 6-membered heterocyclyl ring, wherein said 5-or 6-membered heterocyclyl ring comprising two oxygen atoms as ring member (s) and said 5-or 6-membered heterocyclyl ring is optionally substituted with one or two C 1-6 alkyl, preferably two C 1-6 alkyl, more preferably two methyl, most preferably two methyl on the same carbon atom.
- Cy 1 is a 7-to 14-membered bicyclic heteroaryl which is a pyridinyl ring fused with 1, 4-dioxane ring, wherein said 1, 4-dioxane ring is optionally substituted with one or two C 1-6 alkyl, preferably two C 1-6 alkyl, more preferably two methyl, most preferably two methyl on the same carbon atom.
- Cy 1 is preferably
- Cy 1 is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
- the compound is selected from the exemplified compounds in Examples.
- composition comprising one or more compounds in the present disclosure or a stereoisomer or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.
- TYK2 activity TYK2-related diseases
- a method for treating a disease associated with undesirable TYK2 activity comprising administrating to a subject in need of such treatment a therapeutically effective amount of the compounds in the present disclosure or a stereoisomer or pharmaceutically acceptable salt thereof.
- the disease is inflammatory or autoimmune.
- alkyl refers to a hydrocarbon group selected from linear and branched saturated hydrocarbon groups comprising from 1 to 18, such as from 1 to 12, further such as from 1 to 10, more further such as from 1 to 8, or from 1 to 6, or from 1 to 4, carbon atoms.
- alkyl groups comprising from 1 to 6 carbon atoms include, but not limited to, methyl, ethyl, 1-propyl or n-propyl ( “n-Pr” ) , 2-propyl or isopropyl ( “i-Pr” ) , 1-butyl or n-butyl ( “n-Bu” ) , 2-methyl-1-propyl or isobutyl ( “i-Bu” ) , 1-methylpropyl or s-butyl ( “s-Bu” ) , 1, 1-dimethylethyl or t-butyl ( “t-Bu” ) , 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-penty
- halogen refers to fluoro (F) , chloro (Cl) , bromo (Br) and iodo (I) .
- haloalkyl refers to an alkyl group in which one or more hydrogen is/are replaced by one or more halogen atoms such as fluoro, chloro, bromo, and iodo.
- haloalkyl include haloC 1-8 alkyl, haloC 1-6 alkyl or halo C 1-4 alkyl, but not limited to -CF 3 , -CH 2 Cl, -CH 2 CF 3 , -CCl 2 , CF 3 , and the like.
- alkyloxy refers to an alkyl group as defined above attached to the parent molecular moiety through an oxygen atom.
- alkyloxy e.g., C 1-6 alkyloxy or C 1-4 alkyloxy
- examples of an alkyloxy include, but not limited to, methoxy, ethoxy, isopropoxy, propoxy, n-butoxy, tert-butoxy, pentoxy and hexoxy and the like.
- alkoxy-alkyl- refers to an alkyl group as defined above further substituted with an alkoxy as defined above.
- alkoxy-alkyl- e.g., C 1 - 8 alkoxy-C 1 - 8 alkyl-or C 1 - 6 alkoxy-C 1-6 alkyl-include, but not limited to, methoxymethyl, ethoxymethyl, ethoxyethyl, isopropoxymethyl, or propoxymethyl and the like.
- amino refers to —NH 2 .
- alkylamino refers to -NH (alkyl) .
- dialkylamino refers to -N (alkyl) 2 .
- alkenyl group e.g., C2-6 alkenyl
- examples of the alkenyl group, e.g., C2-6 alkenyl include, but not limited to ethenyl or vinyl, prop-1-enyl, prop-2-enyl, 2-methylprop-1-enyl, but-1-enyl, but-2-enyl, but-3-enyl, buta-1, 3-dienyl, 2-methylbuta-1, 3-dienyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, and hexa-1, 3-dienyl groups.
- alkynyl herein refers to a hydrocarbon group selected from linear and branched hydrocarbon group, comprising at least one C ⁇ C triple bond and from 2 to 18, such as 2 to 8, further such as from 2 to 6, carbon atoms.
- alkynyl group e.g., C2-6 alkynyl
- examples of the alkynyl group, e.g., C2-6 alkynyl include, but not limited to ethynyl, 1-propynyl, 2-propynyl (propargyl) , 1-butynyl, 2-butynyl, and 3-butynyl groups.
- cycloalkyl refers to a hydrocarbon group selected from saturated cyclic hydrocarbon groups, comprising monocyclic and polycyclic (e.g., bicyclic and tricyclic) groups including fused, bridged or spiro cycloalkyl.
- the cycloalkyl group may comprise from 3 to 12, such as from 3 to 10, further such as 3 to 8, further such as 3 to 6, 3 to 5, or 3 to 4 carbon atoms.
- the cycloalkyl group may be selected from monocyclic group comprising from 3 to 12, such as from 3 to 10, further such as 3 to 8, 3 to 6 carbon atoms.
- Examples of the monocyclic cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, 1-cyclopent-1-enyl, 1-cyclopent-2-enyl, 1-cyclopent-3-enyl, cyclohexyl, 1-cyclohex-1-enyl, 1-cyclohex-2-enyl, 1-cyclohex-3-enyl, cyclohexadienyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, and cyclododecyl groups.
- Examples of the saturated monocyclic cycloalkyl group include, but not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.
- the cycloalkyl is a monocyclic ring comprising 3 to 6 carbon atoms (abbreviated as C 3-6 cycloalkyl) , including but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
- bicyclic cycloalkyl groups include those having from 7 to 12 ring atoms arranged as a fused bicyclic ring selected from [4, 4] , [4, 5] , [5, 5] , [5, 6] and [6, 6] ring systems, or as a bridged bicyclic ring selected from bicyclo [2.2.1] heptane, bicyclo [2.2.2] octane, and bicyclo [3.2.2] nonane.
- bicyclic cycloalkyl groups include those arranged as a bicyclic ring selected from [5, 6] and [6, 6] ring systems.
- cycloalkenyl refers to non-aromatic cyclic alkyl groups of from 3 to 10 carbon atoms having single or multiple rings and having at least one double bond and preferably from 1 to 2 double bonds.
- the cycloalkenyl is cyclopentenyl or cyclohexenyl, preferably cyclohexenyl.
- cycloalkynyl refers to non-aromatic cycloalkyl groups of from 5 to 10 carbon atoms having single or multiple rings and having at least one triple bond.
- deuterated is used herein to modify a chemical structure or an organic group or radical, wherein one or more carbon-bound hydrogen (s) are replaced by one or more deuterium (s) , e.g., “deuterated-alkyl” , “deuterated-cycloalkyl” , “deuterated-heterocycloalkyl” , “deuterated-aryl” , “deuterated-morpholinyl” , and the like.
- deuterated-alkyl defined above refers to an alkyl group as defined herein, wherein at least one hydrogen atom bound to carbon is replaced by a deuterium.
- a deuterated alkyl group at least one carbon atom is bound to a deuterium; and it is possible for a carbon atom to be bound to more than one deuterium; it is also possible that more than one carbon atom in the alkyl group is bound to a deuterium.
- aryl used alone or in combination with other terms refers to a group selected from:
- bicyclic ring systems such as 7 to 12 membered bicyclic ring systems, wherein at least one ring is carbocyclic and aromatic, e.g., naphthyl and indanyl; and,
- tricyclic ring systems such as 10 to 15 membered tricyclic ring systems wherein at least one ring is carbocyclic and aromatic, e.g., fluorenyl.
- a monocyclic or bicyclic aromatic hydrocarbon ring has 5 to 10 ring-forming carbon atoms (i.e., C5-10 aryl) .
- Examples of a monocyclic or bicyclic aromatic hydrocarbon ring include, but not limited to, phenyl, naphth-1-yl, naphth-2-yl, anthracenyl, phenanthrenyl, and the like.
- the aromatic hydrocarbon ring is a naphthalene ring (naphth-1-yl or naphth-2-yl) or phenyl ring.
- the aromatic hydrocarbon ring is a phenyl ring.
- heteroaryl herein refers to a group selected from:
- - 7-to 12-membered bicyclic rings comprising at least one heteroatom, for example, from 1 to 4, or, in some embodiments, from 1 to 3, or, in other embodiments, 1 or 2, heteroatoms, selected from nitrogen, oxygen or optionally oxidized sulfur as ring member (s) , with the remaining ring atoms being carbon and wherein at least one ring is aromatic and at least one heteroatom is present in the aromatic ring; and
- - 11-to 14-membered tricyclic rings comprising at least one heteroatom, for example, from 1 to 4, or in some embodiments, from 1 to 3, or, in other embodiments, 1 or 2, heteroatoms, selected from nitrogen, oxygen or optionally oxidized sulfur as ring member (s) , with the remaining ring atoms being carbon and wherein at least one ring is aromatic and at least one heteroatom is present in an aromatic ring.
- the total number of S and O atoms in the heteroaryl group exceeds 1, those heteroatoms are not adjacent to one another. In some embodiments, the total number of S and O atoms in the heteroaryl group is not more than 2. In some embodiments, the total number of S and O atoms in the aromatic heterocycle is not more than 1.
- the heteroaryl group contains more than one heteroatom ring member, the heteroatoms may be the same or different. The nitrogen atoms in the ring (s) of the heteroaryl group can be oxidized to form N-oxides.
- oxidized sulfur refers to S, SO or SO2.
- a monocyclic or bicyclic aromatic heterocyclic ring has 5-, 6-, 7-, 8-, 9-or 10-ring forming members with 1, 2, 3, or 4 heteroatom ring members independently selected from nitrogen (N) , sulfur (S) and oxygen (O) and the remaining ring members being carbon.
- the monocyclic or bicyclic aromatic heterocyclic ring is a monocyclic or bicyclic ring comprising 1 or 2 heteroatom ring members independently selected from nitrogen (N) , sulfur (S) and oxygen (O) .
- the monocyclic or bicyclic aromatic heterocyclic ring is a 5-to 6-membered heteroaryl ring, which is monocyclic and which has 1 or 2 heteroatom ring members independently selected from nitrogen (N) , sulfur (S) and oxygen (O) .
- the monocyclic or bicyclic aromatic heterocyclic ring is an 8-to 10-membered heteroaryl ring, which is bicyclic and which has 1 or 2 heteroatom ring members independently selected from nitrogen, sulfur and oxygen.
- heteroaryl group or the monocyclic or bicyclic aromatic heterocyclic ring examples include, but are not limited to, (as numbered from the linkage position assigned priority 1) pyridyl (such as 2-pyridyl, 3-pyridyl, or 4-pyridyl) , cinnolinyl, pyrazinyl, 2, 4-pyrimidinyl, 3, 5-pyrimidinyl, 2, 4-imidazolyl, imidazopyridinyl, isoxazolyl, oxazolyl, thiazolyl, isothiazolyl, thiadiazolyl (such as 1, 2, 3-thiadiazolyl, 1, 2, 4-thiadiazolyl, or 1, 3, 4-thiadiazolyl) , tetrazolyl, thienyl (such as thien-2-yl, thien-3-yl) , triazinyl, benzothienyl, furyl or furanyl, benzofuryl, benzoimidazo
- heteroaryl which is further fused with a “Heterocyclyl” is defined as a “heteroaryl” .
- Heterocyclyl, " “heterocycle” or “heterocyclic” are interchangeable and refer to a non-aromatic heterocyclyl group comprising one or more heteroatoms selected from nitrogen, oxygen or optionally oxidized sulfur as ring members, with the remaining ring members being carbon, including monocyclic, fused, bridged, and spiro ring, i.e., containing monocyclic heterocyclyl, bridged heterocyclyl, spiro heterocyclyl, and fused heterocyclic groups.
- monocyclic heterocyclyl refers to monocyclic groups in which at least one ring member is a heteroatom selected from nitrogen, oxygen or optionally oxidized sulfur.
- a heterocycle may be saturated or partially saturated.
- Exemplary monocyclic 4 to 9-membered heterocyclyl groups include, but not limited to, (as numbered from the linkage position assigned priority 1) pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, imidazolidin-2-yl, imidazolidin-4-yl , pyrazolidin-2-yl, pyrazolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, 2, 5-piperazinyl, pyranyl, morpholinyl, morpholino, morpholin-2-yl, morpholin-3-yl, oxiranyl, aziridin-1-yl, aziridin-2-yl, azocan-1-yl, azocan-2-yl, azocan-3-yl, azocan-4-yl, azocan-5-yl, thiiranyl, azeti
- spiro heterocyclyl refers to a 5 to 20-membered polycyclic heterocyclyl with rings connected through one common carbon atom (called a spiro atom) , comprising one or more heteroatoms selected from nitrogen, oxygen or optionally oxidized sulfur as ring members, with the remaining ring members being carbon.
- a spiro heterocyclyl group may contain one or more double bonds, but none of the rings has a completely conjugated pi-electron system.
- a spiro heterocyclyl is 6 to 14-membered, and more preferably 7 to 12-membered.
- a spiro heterocyclyl is divided into mono-spiro heterocyclyl, di-spiro heterocyclyl, or poly-spiro heterocyclyl, and preferably refers to mono-spiro heterocyclyl or di-spiro heterocyclyl, and more preferably 4-membered/4-membered, 3-membered/5-membered, 4-membered/5-membered, 4-membered/6-membered, 5-membered/5-membered, or 5-membered/6-membered mono-spiro heterocyclyl.
- fused heterocyclic group refers to a 5 to 20-membered polycyclic heterocyclyl group, wherein each ring in the system shares an adjacent pair of atoms (carbon and carbon atoms or carbon and nitrogen atoms) with another ring, comprising one or more heteroatoms selected from nitrogen, oxygen or optionally oxidized sulfur as ring members, with the remaining ring members being carbon.
- One or more rings of a fused heterocyclic group may contain one or more double bonds, but none of the rings has a completely conjugated pi-electron system.
- a fused heterocyclyl is 6 to 14-membered, and more preferably 7 to 10-membered.
- a fused heterocyclyl is divided into bicyclic, tricyclic, tetracyclic, or polycyclic fused heterocyclyl, preferably refers to bicyclic or tricyclic fused heterocyclyl, and more preferably 5-membered/5-membered, or 5-membered/6-membered bicyclic fused heterocyclyl.
- fused heterocycles include, but not limited to, the following groups octahydrocyclopenta [c] pyrrole (e.g., octahydrocyclopenta [c] pyrrol-2-yl) , octahydropyrrolo [3, 4-c] pyrrolyl, octahydroisoindolyl, isoindolinyl (e.g., isoindoline-2-yl) , octahydro-benzo [b] [1, 4] dioxin.
- octahydrocyclopenta [c] pyrrole e.g., octahydrocyclopenta [c] pyrrol-2-yl
- octahydropyrrolo [3, 4-c] pyrrolyl octahydroisoindolyl
- isoindolinyl e.g., isoindoline-2-yl
- bridged heterocyclyl refers to a 5-to 14-membered polycyclic heterocyclic alkyl group, wherein every two rings in the system share two disconnected atoms, comprising one or more heteroatoms selected from nitrogen, oxygen or optionally oxidized sulfur as ring members, with the remaining ring members being carbon.
- One or more rings of a bridged heterocyclyl group may contain one or more double bonds, but none of the rings has a completely conjugated pi-electron system.
- a bridged heterocyclyl is 6 to 14-membered, and more preferably 7 to 10-membered.
- a bridged heterocyclyl is divided into bicyclic, tricyclic, tetracyclic or polycyclic bridged heterocyclyl, and preferably refers to bicyclic, tricyclic or tetracyclic bridged heterocyclyl, and more preferably bicyclic or tricyclic bridged heterocyclyl.
- Representative examples of bridged heterocyclyls include, but not limited to, the following groups: 2-azabicyclo [2.2.1] heptyl, azabicyclo [3.1.0] hexyl, 2-azabicyclo [2.2.2] octyl and 2-azabicyclo [3.3.2] decyl.
- Enantiomers refer to two stereoisomers of a compound which are non-superimposable mirror images of one another. Where the compounds disclosed herein possess two or more asymmetric centers, they may additionally exist as diastereomers. Enantiomers and diastereomers fall within the broader class of stereoisomers. All such possible stereoisomers as substantially pure resolved enantiomers, racemic mixtures thereof, as well as mixtures of diastereomers are intended to be included. All stereoisomers of the compounds disclosed herein and /or pharmaceutically acceptable salts thereof are intended to be included. Unless specifically mentioned otherwise, reference to one isomer applies to any of the possible isomers. Whenever the isomeric composition is unspecified, all possible isomers are included.
- the term “substantially pure” as used herein means that the target stereoisomer contains no more than 35%, such as no more than 30%, further such as no more than 25%, even further such as no more than 20%, by weight of any other stereoisomer (s) . In some embodiments, the term “substantially pure” means that the target stereoisomer contains no more than 10%, for example, no more than 5%, such as no more than 1%, by weight of any other stereoisomer (s) .
- substituents found on cyclohexyl or cyclobutyl ring may adopt cis and trans formations.
- Cis formation means that both substituents are found on the upper side of the 2 substituent placements on the carbon, while trans would mean that they were on opposing sides.
- reaction products from one another and /or from starting materials.
- the desired products of each step or series of steps is separated and /or purified (hereinafter separated) to the desired degree of homogeneity by the techniques common in the art.
- separations involve multiphase extraction, crystallization from a solvent or solvent mixture, distillation, sublimation, or chromatography.
- Chromatography can involve any number of methods including, for example: reverse-phase and normal phase; size exclusion; ion exchange; high, medium and low pressure liquid chromatography methods and apparatus; small scale analytical; simulated moving bed ( "SMB” ) and preparative thin or thick layer chromatography, as well as techniques of small scale thin layer and flash chromatography.
- SMB simulated moving bed
- Diastereomers refers to stereoisomers of a compound with two or more chiral centers but which are not mirror images of one another. Diastereomeric mixtures can be separated into their individual diastereomers on the basis of their physical chemical differences by methods well known to those skilled in the art, such as by chromatography and /or fractional crystallization.
- Enantiomers can be separated by converting the enantiomeric mixture into a diastereomeric mixture by reaction with an appropriate optically active compound (e.g., chiral auxiliary such as a chiral alcohol or Mosher’s acid chloride) , separating the diastereomers and converting (e.g., hydrolyzing) the individual diastereoisomers to the corresponding pure enantiomers.
- an appropriate optically active compound e.g., chiral auxiliary such as a chiral alcohol or Mosher’s acid chloride
- Enantiomers can also be separated by use of a chiral HPLC column.
- a single stereoisomer e.g., a substantially pure enantiomer
- Racemic mixtures of chiral compounds of the invention can be separated and isolated by any suitable method, including: (1) formation of ionic, diastereomeric salts with chiral compounds and separation by fractional crystallization or other methods, (2) formation of diastereomeric compounds with chiral derivatizing reagents, separation of the diastereomers, and conversion to the pure stereoisomers, and (3) separation of the substantially pure or enriched stereoisomers directly under chiral conditions. See: Wainer, Irving W., Ed. Drug Stereochemistry: Analytical Methods and Pharmacology. New York: Marcel Dekker, Inc., 1993.
- “Pharmaceutically acceptable salts” refers to those salts which are, within the scope of sound medical judgment, suitable for use in contact with the tissues of humans and lower animals without undue toxicity, irritation, allergic response and the like, and are commensurate with a reasonable benefit/risk ratio.
- a pharmaceutically acceptable salt may be prepared in situ during the final isolation and purification of the compounds disclosed herein, or separately by reacting the free base function with a suitable organic acid or by reacting the acidic group with a suitable base.
- the free base can be obtained by basifying a solution of the acid salt.
- an addition salt such as a pharmaceutically acceptable addition salt, may be produced by dissolving the free base in a suitable organic solvent and treating the solution with an acid, in accordance with conventional procedures for preparing acid addition salts from base compounds.
- a pharmaceutically acceptable salt thereof include salts of at least one compound of Formula (I) , and salts of the stereoisomers of the compound of Formula (I) , such as salts of enantiomers, and /or salts of diastereomers.
- administration when applied to an animal, human, experimental subject, cell, tissue, organ, or biological fluid, mean contact of an exogenous pharmaceutical, therapeutic, diagnostic agent, or composition to the animal, human, subject, cell, tissue, organ, or biological fluid.
- Treatment of a cell encompasses contact of a reagent to the cell, as well as contact of a reagent to a fluid, where the fluid is in contact with the cell.
- administration and “treatment” also means in vitro and ex vivo treatments, e.g., of a cell, by a reagent, diagnostic, binding compound, or by another cell.
- subject herein includes any organism, preferably an animal, more preferably a mammal (e.g., rat, mouse, dog, cat, rabbit) and most preferably a human.
- an effective amount refers to an amount of the active ingredient, such as compound that, when administered to a subject for treating a disease, or at least one of the clinical symptoms of a disease or disorder, is sufficient to affect such treatment for the disease, disorder, or symptom.
- the “therapeutically effective amount” can vary with the compound, the disease, disorder, and/or symptoms of the disease or disorder, severity of the disease, disorder, and/or symptoms of the disease or disorder, the age of the subject to be treated, and/or the weight of the subject to be treated. An appropriate amount in any given instance can be apparent to those skilled in the art or can be determined by routine experiments.
- “therapeutically effective amount” is an amount of at least one compound and /or at least one stereoisomer thereof, and /or at least one pharmaceutically acceptable salt thereof disclosed herein effective to “treat” as defined above, a disease or disorder in a subject.
- the “therapeutically effective amount” refers to the total amount of the combination objects for the effective treatment of a disease, a disorder or a condition.
- the pharmaceutical composition comprising the compound disclosed herein can be administrated via oral, inhalation, rectal, parenteral or topical administration to a subject in need thereof.
- the pharmaceutical composition may be a regular solid Formulation such as tablets, powder, granule, capsules and the like, a liquid Formulation such as water or oil suspension or other liquid Formulation such as syrup, solution, suspension or the like; for parenteral administration, the pharmaceutical composition may be solution, water solution, oil suspension concentrate, lyophilized powder or the like.
- the Formulation of the pharmaceutical composition is selected from tablet, coated tablet, capsule, suppository, nasal spray or injection, more preferably tablet or capsule.
- the pharmaceutical composition can be a single unit administration with an accurate dosage.
- the pharmaceutical composition may further comprise additional active ingredients.
- compositions disclosed herein can be produced by the conventional methods in the pharmaceutical field.
- the active ingredient can be mixed with one or more excipients, then to make the desired Formulation.
- the “pharmaceutically acceptable excipient” refers to conventional pharmaceutical carriers suitable for the desired pharmaceutical Formulation, for example: a diluent, a vehicle such as water, various organic solvents, etc., a filler such as starch, sucrose, etc.
- a binder such as cellulose derivatives, alginates, gelatin and polyvinylpyrrolidone (PVP) ; a wetting agent such as glycerol; a disintegrating agent such as agar, calcium carbonate and sodium bicarbonate; an absorption enhancer such as quaternary ammonium compound; a surfactant such as hexadecanol; an absorption carrier such as Kaolin and soap clay; a lubricant such as talc, calcium stearate, magnesium stearate, polyethylene glycol, etc.
- PVP polyvinylpyrrolidone
- the pharmaceutical composition further comprises other pharmaceutically acceptable excipients such as a decentralized agent, a stabilizer, a thickener, a complexing agent, a buffering agent, a permeation enhancer, a polymer, aromatics, a sweetener, and a dye.
- other pharmaceutically acceptable excipients such as a decentralized agent, a stabilizer, a thickener, a complexing agent, a buffering agent, a permeation enhancer, a polymer, aromatics, a sweetener, and a dye.
- disease refers to any disease, discomfort, illness, symptoms or indications, and can be interchangeable with the term “disorder” or “condition” .
- Cn-m indicates a range which includes the endpoints, wherein n and m are integers and indicate the number of carbons. Examples include C1-8, C1-6, and the like.
- reaction flasks were fitted with rubber septa for the introduction of substrates and reagents via syringe; and glassware was oven dried and/or heat dried.
- reaction flasks were fitted with rubber septa for the introduction of substrates and reagents via syringe; and glassware was oven dried and /or heat dried.
- column chromatography purification was conducted on a Biotage system (Manufacturer: Dyax Corporation) having a silica gel column or on a silica SepPak cartridge (Waters) , or was conducted on a Teledyne Isco Combiflash purification system using prepacked silica gel cartridges.
- 1 H NMR spectra were recorded on a Varian instrument operating at 400 MHz. 1 H-NMR spectra were obtained using CDCl 3 , CD 2 Cl 2 , CD 3 OD, D 2 O, d 6 -DMSO, d 6 -acetone or (CD 3 ) 2 CO as solvent and tetramethylsilane (0.00 ppm) or residual solvent (CDCl 3 : 7.25 ppm; CD 3 OD: 3.31 ppm; D 2 O: 4.79 ppm; d 6 -DMSO: 2.50 ppm; d 6 -acetone: 2.05; (CD 3 ) 2 CO: 2.05) as the reference standard.
- Step 1 2, 6-dibromo-4- (bromomethyl) pyridine
- Step 4 2-bromo-6-methanesulfonyl-4- (methoxymethyl) pyridine
- Example BB2 Synthesis of 2-bromo-4- [2- [ (tert-butyldimethylsilyl) oxy] ethoxy] -6-methanesulfonyl pyridine
- Step 3 2-bromo-4- [2- [ (tert-butyldimethylsilyl) oxy] ethoxy] -6-methanesulfonylpyridine
- Example BB3 Synthesis of 2-bromo-4- ( (2, 2-dimethyl-1, 3-dioxolan-4-yl) methoxy) -6- (methyl sulfonyl) pyridine
- Example BB4 Synthesis of 2-bromo-4- (2- ( (tert-butyldimethylsilyl) oxy) propoxy) -6- (methylsulfonyl) pyridine
- Step 1 1- ( (2-Bromo-6- (methylsulfonyl) pyridin-4-yl) oxy) propan-2-ol
- Step 2 2-Bromo-4- (2- ( (tert-butyldimethylsilyl) oxy) propoxy) -6- (methylsulfonyl) pyridine
- Step 1 2, 6-dibromo-4- (2-methoxyethoxy) pyridine
- Step 2 6-bromo-4- (2-methoxyethoxy) pyridine-2-sulfonyl chloride
- Step 3 6-bromo-4- (2-methoxyethoxy) pyridine-2-sulfonamide
- Step 3 2, 6-dibromo-4- (difluoromethyl) pyridine
- Step 5 2-bromo-4- (difluoromethyl) -6- (methylsulfonyl) pyridine
- Example BB18 Synthesis of [2- (3-bromo-5-methanesulfonylphenoxy) ethoxy] (tert-butyl) dimethylsilane
- Step 1 tert-butyl [2- (3, 5-dibromophenoxy) ethoxy] dimethylsilane
- Step 2 [2- [3-bromo-5- (methylsulfanyl) phenoxy] ethoxy] (tert-butyl) dimethylsilane
- Step 1 (3-bromo-5-methoxyphenyl) (methyl) sulfane
- Step 1 (3-bromo-5-methylphenyl) (methyl) sulfane
- Step 2 2-bromo-3-isopropoxy-6- (methylsulfanyl) pyridine
- Example BB35 Synthesis of 1-bromo-3- (cyclopropylmethoxy) -5- (methylsulfonyl) benzene
- Step 1 1, 3-dibromo-5- (cyclopropylmethoxy) benzene
- Step 2 (3-bromo-5- (cyclopropylmethoxy) phenyl) (methyl) sulfane
- Step 3 1-bromo-3- (cyclopropylmethoxy) -5- (methylsulfonyl) benzene
- Step 4 2, 6-dibromo-4- (1-methoxyethyl) pyridine
- Step 5 2-bromo-4- (1-methoxyethyl) -6- (methylthio) pyridine
- Step 6 2-bromo-4- (1-methoxyethyl) -6- (methylsulfonyl) pyridine
- Step 3 tert-butyl ( [ [ (2R) -1- (3, 5-dibromophenoxy) propan-2-yl] oxy] ) dimethylsilane
- Step 4 [ [ (2R) -1- [3-bromo-5- (methylsulfanyl) phenoxy] propan-2-yl] oxy] (tert-butyl) dimethylsilane
- Step 5 [ [ (2R) -1- (3-bromo-5-methanesulfonylphenoxy) propan-2-yl] oxy] (tert-butyl) dimethylsilane
- Example BB45 Synthesis of [ [ (2S) -1- (3-bromo-5-methanesulfonylphenoxy) propan-2- yl] oxy] (tert-butyl) dimethylsilane
- Step 3 tert-butyl ( [ [ (2S) -1- (3, 5-dibromophenoxy) propan-2-yl] oxy] ) dimethylsilane
- Step 4 [ [ (2S) -1- [3-bromo-5- (methylsulfanyl) phenoxy] propan-2-yl] oxy] (tertbutyl) dimethylsilane
- Step 5 [ [ (2S) -1- (3-bromo-5-methanesulfonylphenoxy) propan-2-yl] oxy] (tert-butyl) dimethylsilane
- Step 2 2-bromo-3- (difluoromethoxy) -6- (methylsulfanyl) pyridine
- Step 1 (R) -2-methoxypropyl 4-methylbenzenesulfonate
- Step 2 (R) -2, 6-dibromo-4- (2-methoxypropoxy) pyridine
- Step 3 (R) -2-bromo-4- (2-methoxypropoxy) -6- (methylthio) pyridine
- Step 4 (R) -2-bromo-4- (2-methoxypropoxy) -6- (methylsulfonyl) pyridine
- Step 1 6-bromo-3-methoxy-2- (methylthio) pyridine
- Step 2 6-bromo-3-methoxy-2- (methylsulfonyl) pyridine
- 6-bromo-3-methoxy-2- (methylsulfanyl) pyridine (1.00 g, 4.27 mmol)
- THF 10 mL
- H 2 O 10 mL
- NaIO 4 3.65 g, 17.07 mmol
- RuCl 3 3 .
- H 2 O (192.59 mg, 0.85 mmol)
- the resulting solution was stirred for 1 h at 0 °C.
- the resulting solution was diluted with EA (100 mL) .
- the resulting mixture was washed with H 2 O (100 mL x 3) .
- Step 2 2-bromo-4-methyl-6- (methylsulfonyl) pyridine
- Step 1 2-chloro-6- (methylsulfanyl) -4- (trifluoromethyl) pyridine
- Step 2 Synthesis of 2, 6-dibromo-4- (3, 6-dihydro-2H-pyran-4-yl) pyridine
- Step 3 Synthesis of 2, 6-dibromo-4- (tetrahydro-2H-pyran-4-yl) pyridine
- Step 4 Synthesis of 2-bromo-6- (methylthio) -4- (tetrahydro-2H-pyran-4-yl) pyridine
- Step 5 Synthesis of 2-bromo-6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-4-yl) pyridine
- Step: 3 2-bromo-3, 4-dimethoxy-6- (methylsulfonyl) pyridine
- Example BB60 Synthesis of (R and S) -2-chloro-4- (1-methoxyethyl) -6- (methylsulfonyl) pyridine
Abstract
Description
Claims (21)
- A compound of Formula (I)or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein:X is N or CH;Y is N, NR 3 or CR 3;L 1 is a direct bond, - (CR aR b) q-, -O-, -S-, -S (O) -, -SO 2-, -C (O) -, C (O) O-, -OC (O) -, -NR a-, -O- (CR aR b) q-, -S- (CR aR b) q-, -S (O) - (CR aR b) q-, -SO 2- (CR aR b) q-, -C (O) - (CR aR b) q-, C (O) O- (CR aR b) q-, -OC (O) - (CR aR b) q-, -NR a- (CR aR b) q-, -C (O) NR a-, -NR aC (O) -, -NR aC (O) O-, -NR aC (O) NR b-, -SO 2NR a-, -NR aSO 2-, -NR aS (O) 2NR b-, -NR aS (O) NR b-, -C (O) NR aSO 2-, -C (O) NR aSO-, or -C (=NR a) NR b-, wherein q is a number of 1 to 7, and,R a and R b are independently hydrogen, -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;R 1 is -C 1-6alkyl, -haloC 1-6alkyl, -C 1-6 alkoxy, -haloC 1-6 alkoxyl, -C 3-6 cycloalkyl, aryl, or -NR cR d;each of R 2, R 3, and R 4 is independently hydrogen, cyano, halogen, -C 1-6alkyl, -C 2-6alkenyl, -C 2- 6alkynyl, -C 3-8cycloalkyl, heterocyclyl, aryl, heteroaryl, oxo, -NO 2, -OR e, -SO 2R e, -COR e, -CO 2R e, -CONR eR f, -C (=NR e) NR fR g, -NR eR f, -NR eCOR f, -NR eCONR fR g, -NR eCO 2R f, -NR eSONR fR g, -NR eSO 2NR fR g, or –NR eSO 2R f,wherein each of -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, -C 3-8cycloalkyl, heterocyclyl, aryl, or heteroaryl is independently and optionally substituted with at least one substituent selected fromi) cyano, -oxo-, halogen, -NR mR n, -OR h, -C (O) NR mR n;ii) heterocyclyl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR mR n, substituted or unsubstituted -C 1-6alkyl, substituted or unsubstituted -C 1- 6alkoxy or -C (O) NR mR; or,iii) C 1-6alkyl optionally substituted with at least one substitution independently selected from cyano, halogen, hydroxy, --NH 2or C 1-6alkoxy;wherein R h is hydrogen, hydroxy, -NH 2, -C 1-6alkyl, C 1-6alkyl substituted with hydroxy, or heterocyclyl,R e, R f, and R g are each independently hydrogen, -C 1-6alkyl, -C 1-6alkoxy, -C 2-6alkenyl, -C 2-6alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein each of -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally independently substituted with one to three substituents selected from cyano, -oxo-, halogen, hydroxy, -NR mR n, -C 1-6alkyl, -C 1-6alkoxy, -C 3-6cycloalkyl optionally substituted with halogen, hydroxy or -C 1-6alkoxy, -C (O) NR mR n, or heterocyclyl;R 5 is hydrogen or C 1-6alkyl;Cy 1 is 6-to 12-membered aryl or 5-to 14-membered heteroaryl, or 5-to 14-membered heterocyclyl, each of which is optionally substituted with at least one substituent R i,R i is independently halogen, cyano, -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, -C 3-8cycloalkyl, heterocyclyl, aryl, heteroaryl, oxo, cyano (-CN) , -NO 2, -OR j, -SO 2R j, -COR j, -CO 2R k, -CONR jR k, -C (=NR j) NR kR l, -NR jR k, -NR jCOR k, -NR jCONR kR l, -NR jCO 2R k, -NR jSONR kR l, -NR jSO 2NR kR l, or –NR jSO 2R k, wherein each of -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, -C 3-8cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with halogen, -OR m, -C (O) R m, -NR mR n, -C 1-6alkyl, C 1-6alkoxy-, C 1-6alkyl substituted with -C 1-6alkoxy or -oxo-;R j, R k, R l, R m, R n are each independently hydrogen, -C 1-6alkyl, C 1-6alkoxy-C 1-6alkyl-, -C 2-6alkenyl, -C 2- 6alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;or (R 1 and R 2) , or (R 2 and R 3) , or (R 3 and R 4) , together with the atoms to which they are attached, form a fused ring system, said fused ring system comprises 0-4 heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) and is optionally and independently substituted with halogen, -C 1-6alkyl, -C 1-6alkoxy, C 1-6alkyl substituted with halogen, C 1-6alkoxy substituted with halogen or -C 3- 6cycloalkyl;any of the said alkyl or alkoxy is optionally enriched in deuterium.
- The compound of claim 1, wherein Y is CR 3.
- The compound of claim 1, wherein the compound is Formula (I-A)or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein:X is N or CH;L 1 is a direct bond, - (CR aR b) q-, -O-, -S-, -S (O) -, -SO 2-, -C (O) -, C (O) O-, -OC (O) -, -NR a-, -O- (CR aR b) q-, -S- (CR aR b) q-, -S (O) - (CR aR b) q-, -SO 2- (CR aR b) q-, -C (O) - (CR aR b) q-, C (O) O- (CR aR b) q-, -OC (O) - (CR aR b) q-, -NR a- (CR aR b) q-, -C (O) NR a-, -NR aC (O) -, -NR aC (O) O-, -NR aC (O) NR b-, -SO 2NR a-, -NR aSO 2-, -NR aS (O) 2NR b-, -NR aS (O) NR b-, -C (O) NR aSO 2-, -C (O) NR aSO-, or -C (=NR a) NR b-, wherein q is a number of 1 to 7, and ,R a and R b are independently hydrogen, -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;R 1 is -C 1-6alkyl, -haloC 1-6alkyl, -C 1-6 alkoxy, -haloC 1-6 alkoxyl, -C 3-6 cycloalkyl, aryl, or -NR mR n;each of R 2, R 3, and R 4 is independently hydrogen, halogen, -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, -C 3- 8cycloalkyl, heterocyclyl, aryl, heteroaryl, -oxo-, -CN, -NO 2, -OR e, -SO 2R e, -COR e, -CO 2R e, -CONR eR f, -C (=NR e) NR fR g, -NR eR f, -NR eCOR f, -NR eCONR fR g, -NR eCO 2R f, -NR eSONR fR g, -NR eSO 2NR fR g, or –NR eSO 2R f,wherein each of -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, -C 3-8cycloalkyl, heterocyclyl, aryl, or heteroaryl is independently and optionally substituted with at least one substituents selected from cyano, oxo, halogen, C 1-6alkyl optionally substituted with halogen, -C 1-6alkyl substituted with hydroxy (preferably, hydroxymethyl, hydroxyethyl) , -OR h, -C (O) NR mR n, -NH 2, C 1-6alkyl substituted with NH 2 or -C 1-6alkyl substituted with C 1-6alkoxy;wherein R h is hydrogen, alkyl, hydroxy-C 1-6alkyl or heterocyclyl,R e, R f, and R g are each independently hydrogen, -C 1-6alkyl, -C 1-6alkoxy, -C 2-6alkenyl, -C 2-6alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein each of -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally independently substituted with one to three substituents selected from halogen, hydroxy, cyano, or -C 1-6alkoxy; -C 3-6cycloalkyl optionally substituted with halogen, hydroxy, or C 1-6alkoxy, or heterocyclyl;R 5 is hydrogen or C 1-6alkyl;Cy 1 is 6-to 12-membered aryl or 5-to 14-membered heteroaryl, or 5-to 14-membered heterocyclyl, each of which is optionally substituted with at least one substituent R i,R i is independently halogen, cyano, -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, -C 3-8cycloalkyl, heterocyclyl, aryl, heteroaryl, oxo, -CN, -NO 2, -OR j, -SO 2R j, -COR j, -CO 2R k, -CONR jR k, -C (=NR j) NR kR l, -NR jR k, -NR jCOR k, -NR jCONR kR l, -NR jCO 2R k, -NR jSONR kR l, -NR jSO 2NR kR l, or –NR jSO 2R k,wherein each of said -C 1-6alkyl, -C 2-6alkenyl, -C 2-6alkynyl, -C 3-8cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with halogen, OR m, C (O) R m, -NR mR n, -C 1-6alkyl, C 1-6alkoxy-, C 1-6alkoxy-C 1- 6alkyl-, or oxo;R j, R k, R l, R m, R n are each independently hydrogen, -C 1-6alkyl, -C 1-6alkyl substituted with C 1-6alkoxy, -C 2-6alkenyl, -C 2-6alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;or (R 1 and R 2) , or (R 2 and R 3) , or (R 3 and R 4) , together with the atoms to which they are attached, form a fused ring system, said fused ring system comprises 0-4 heteroatoms selected from oxygen, nitrogen or sulfur as ring member (s) and is optionally and independently substituted with halogen, -C 1- 6alkyl, -C 1-6alkoxy, -haloC 1-6alkyl, -haloC 1-6alkoxy, or -C 3-6cycloalkyl;any of the said alkyl or alkoxy is optionally enriched in deuterium.
- The compound of any one of claims 1-3, wherein R 1 is -C 1-3 alkyl, -NR cR d or -C 3-6 cycloalkyl, preferably -NH 2, methyl, ethyl, propyl, isopropyl, cyclopropyl or cyclopentyl.
- The compound of any one of claims 1-3, wherein R 2 and R 4 are each independently hydrogen, halogen, -C 1-6alkyl, or -C 1-6alkoxy, preferably hydrogen, fluoro, methyl, methoxy, ethoxy, or isopropoxy.
- The compound of any one of claims 1-5, wherein R 3 is- hydrogen;- cyano;- halogen;- -C 1-4 alkyl optionally substituted with at least one substituent independently selected from halogen, 3-to 6-membered heterocyclyl or -OR h, wherein3-to 6-membered heterocyclyl comprises one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (O) as ring member (s) , optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR mR n, C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, wherein -C 1-6alkyl or -C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1-6alkoxy; andR h is hydrogen, alkyl, or heterocyclyl;- -C 3-6cycloalkyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR mR n, hydroxy, -C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, wherein -C 1- 6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1-6alkoxy;- heterocyclyl comprising one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , optionally substituted with at least one substituent independently selected from cyano, -oxo-, halogen, hydroxy, C 1-6alkyl, alkoxy, , -NRR mR n, or -C (O) NR mR n, and wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1-6alkoxy;- -OR e, wherein R e is -C 1-6alkyl, -C 3-6cycloalkyl, 3-to 6-membered heterocyclyl , or aryl, whereini) -C 1-6alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR mR n, -C 1-6alkoxy-, -C 3-6cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-6alkyl, C 1-6alkoxy or -C (O) NR mR n, 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, C 1-6alkyl or C 1- 6alkoxy; and,ii) -C 3-6cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, -NR mR n, C 1-6alkyl, C 1-6alkoxy or -C (O) NR mR n, wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1- 6alkoxy;- -C 5-10aryl; or- heteroaryl comprising one oxygen (O) , nitrogen (N) or sulfur (S) heteroatom as ring member, optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, wherein -C 1-6alkyl or C 1- 6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1-6alkoxy;and wherein R m and R n are independently selected from hydrogen or C 1-3alkyl;any of the said alkyl or alkoxy is optionally enriched in deuterium.
- The compound of claim 6, wherein R 3 is- hydrogen;- cyano;- halogen;- -C 1-4 alkyl optionally substituted with at least one substituent independently selected from halogen, 3-to 6-membered heterocyclyl or -OR h, whereinsaid 3-to 6-membered heterocyclyl comprises one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (O) as ring member (s) , optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR mR n, C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1- 6alkyl or C 1-6alkoxy, and,R h is hydrogen, alkyl or heterocyclyl (preferably 3-to 6-membered heterocyclyl, e.g., tetrahydrofuranyl, thiazolidinyl) ;- -C 3-6cycloalkyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR mR n, hydroxy, -C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, wherein -C 1- 6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1-6alkoxy;- heterocyclyl, preferably 4-to 6-membered monocyclic saturated heterocyclyl, saturated mono-spiro heterocyclyl, saturated bicyclic fused heterocyclyl, or saturated bridged heterocyclyl, comprising one or two heteroatoms selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , more preferably morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -C 1-6alkyl, alkoxy, , -NR mR n, or -C (O) NR mR n, and wherein -C 1-6alkyl or -C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1-6alkoxy;- -OR e, wherein R e is -C 1-6alkyl, -C 3-6cycloalkyl, 3-to 6-membered heterocyclyl (preferably 4-to 6-membered monocyclic saturated heterocyclyl comprising one oxygen heteroatom as ring member) , or aryl, whereini) -C 1-6alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR mR n, -C 1-6alkoxy-, -C 3-6cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-6alkyl, C 1-6alkoxy or -C (O) NR mR n, 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, -C 1-6alkyl or -C 1- 6alkoxy; and,ii) -C 3-6cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, NR mR n, C 1-6alkyl, C 1-6alkoxy or -C (O) NR mR n, wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1- 6alkoxy;- -C 5-10aryl; or- heteroaryl, preferably 5-to 6-membered heteroaryl comprising one oxygen (O) , nitrogen (N) or sulfur (S) heteroatom as ring member, optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1-6alkoxy;and wherein R m and R n are independently selected from hydrogen or C 1-3alkyl.
- The compound of claim 6, wherein R 3 is- hydrogen, cyano, halogen;- -C 1-4 alkyl optionally substituted with at least one substituent independently selected from halogen, 3-to 6-membered heterocyclyl or -OR h, whereinsaid 3-to 6-membered heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl, thiazolidinyl or azetidinyl, each of which is optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR mR n, C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1-6alkoxy, and, R h is hydrogen, C 1- 6alkyl or 3-to 6-membered heterocyclyl (e.g., tetrahydrofuranyl or thiazolidinyl) ;- -C 3-6cycloalkyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, NR mR n, hydroxy, -C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, hydroxy, or C 1- 6alkoxy, wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1-6alkoxy;- heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, C 1-6alkyl, alkoxy, -NRR mR n, or -C (O) NR mR n, and wherein -C 1-6alkyl or -C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or -C 1-6alkoxy;- -OR e, wherein R e is -C 1-6alkyl, -C 3-6cycloalkyl, 4-to 6-membered monocyclic saturated heterocyclyl comprising one oxygen heteroatom as ring member, or C 6-10aryl, whereini) -C 1-6alkyl is optionally substituted with deuterium, cyano, -oxo-, halogen, hydroxy, -NR mR n, -C 1-6alkoxy-, -C 3-6cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, -C 1- 6alkyl or -C 1-6alkoxy; and,ii) -C 3-6cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, NR mR n, C 1-6alkyl, C 1-6alkoxy or -C (O) NR mR n, wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1- 6alkoxy;- -C 6-10aryl; or- 5-to 6-membered heteroaryl selected from pyridinyl, pyridazinyl, pyrazinyl, thiazolyl or isoxazolyl, each of which is optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or C 1-6alkoxy;and wherein R m and R n are independently selected from hydrogen or -C 1-3alkyl.-
- The compound of claim 6, wherein R 3 is- hydrogen, cyano, halogen;- -C 1-4 alkyl optionally substituted with at least one substituent independently selected from halogen, hydroxy, C 1-3alkoxy, thiazolidin-3-yl optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -NR mR n, or -C 1-3alkyl;- -C 3-6cycloalkyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR mR n, hydroxy, -C 1-6alkyl, or -C 1-6alkoxy, wherein -C 1-6alkyl or C 1- 6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or -C 1-3alkoxy;- heterocyclyl is selected from morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, 1, 4-dioxanyl, piperidinyl or azetidinyl, optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, C 1-6alkyl, alkoxy, -NR mR n, or -C (O) NR mR n, and wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or -C 1-6alkoxy;- -OR e, wherein R e is -C 1-6alkyl, -C 3-6cycloalkyl, 4-to 6-membered monocyclic saturated heterocyclyl comprising one oxygen heteroatom as ring member, or C 6-10aryl, whereini) -C 1-6alkyl is optionally substituted with cyano, -oxo-, halogen, hydroxy, -NR mR n, -C 1- 6alkoxy-, -C 3-6cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, -C 1-6alkyl or -C 1-6alkoxy; and,ii) -C 3-6cycloalkyl or 3-to 6-membered heterocyclyl is optionally substituted with cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, wherein -C 1- 6alkyl or -C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or -C 1-6alkoxy;- -C 6-10aryl; or- 5-to 6-membered heteroaryl selected from pyridinyl, pyridazinyl, pyrazinyl, thiazolyl or isoxazolyl, each of which is optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-6alkyl, -C 1-6alkoxy or -C (O) NR mR n, wherein -C 1-6alkyl or -C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or -C 1-6alkoxy;and wherein R m and R n are independently selected from hydrogen or -C 1-3alkyl.
- The compound of claim 6, wherein R 3 is- hydrogen, cyano, halogen;- methyl, ethyl, propyl or butyl, each of which optionally substituted with at least one substituent independently selected from halogen, hydroxy, methoxy, ethoxy, propoxy, or 2, 4-dioxothiazolidin-3-yl; cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, -NR mR n, hydroxy, -C 1-3alkyl, or -C 1-3alkoxy, wherein -C 1-3alkyl or C 1-3alkoxy is optionally substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-3alkyl or -C 1-3alkoxy;- heterocyclyl is selected from morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, pyrrolidine-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1, 4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, azetidin-1-yl, azetidine-2-yl, azetidin-3-yl, 5-azaspiro [2.4] heptanyl, 3-azabicyclo [3.1.0] hexan-3-yl or 2-azabicyclo [3.1.0] hexan-2-yl, each of which is optionally substituted with at least one substituent independently selected from cyano, -oxo, halogen, hydroxy, -C 1-6alkyl, -C 1-6alkoxy, -NR mR n, or -C (O) NR mR n, and wherein -C 1-6alkyl or C 1-6alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-6alkyl or -C 1-6alkoxy;- -OR e, wherein R e isi) methyl, ethyl, propyl (iso-propyl) , butyl, pentyl or hexyl, each of which is optionally substituted with deuterium, cyano, -oxo-, halogen, hydroxy, -NR mR n, -C 1-3alkoxy-, -C 3-6cycloalkyl optionally substituted with cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-3alkyl, -C 1-3alkoxy or -C (O) NR mR n, or 4-to 6-membered heterocyclyl optionally substituted with cyano, halogen, hydroxy, -C 1-3alkyl or -C 1- 3alkoxy; or,ii) cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1, 4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, azetidin-1-yl, azetidine-2-yl or azetidin-3-yl, each of which is optionally substituted with cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-3alkyl, -C 1-3alkoxy or -C (O) NR mR n, wherein -C 1-3alkyl or -C 1-3alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-3alkyl or -C 1-3alkoxy;- -C 6-10aryl; or- 5-to 6-membered heteroaryl selected from pyridin-1-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-1-yl, pyridazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-1-yl, pyrazin-2-yl, thiazol-2-yl, thiazol-3-yl, thiazol-4-yl, isoxazol-2-yl, isoxazol-3-yl or isoxazol-4-yl, each of which is optionally substituted with at least one substitution independently selected from cyano, -oxo, halogen, hydroxy, -NR mR n, -C 1-3alkyl, -C 1-3alkoxy or -C (O) NR mR n, wherein -C 1-3alkyl or -C 1- 3alkoxy is substituted with at least one substitution independently selected from cyano, halogen, hydroxy, -NH 2, -C 1-3alkyl or C 1-3alkoxy;and wherein R m and R n are independently selected from hydrogen or -C 1-3alkyl.
- The compound of claim 6, wherein R 3 is- Hydrogen;- Methyl, 1-methoxyethyl, 2-hydroxypropan-2-yl, 1-methoxyethyl, or (2, 4-dioxothiazolidin-3-yl) methyl;- Isopropoxy, methoxy-d3, methoxy, ethoxy, difluoromethoxy, 2-methoxyethoxy, 2-methoxy-2-methylpropoxy, 2-hydroxy-2-methylpropoxy, cyclopropylmethoxy, (1, 4-dioxan-2-yl) methoxy, cyclobutoxy, (4-hydroxycyclohexyl) oxy, (cis-4-hydroxycyclohexyl) oxy, (trans-4-hydroxycyclohexyl) oxy, (4-methoxycyclohexyl) oxy, (cis-4-methoxycyclohexyl) oxy, (trans-4-methoxycyclohexyl) oxy, (3-methyloxetan-3-yl) methoxy, 2-methyl-2-morpholinopropoxy;- cyano- 3-methoxycyclobutyl, (trans) -3-methoxycyclobutyl, (cis) -3-methoxycyclobutyl, 2, 2-dichlorocyclopropyl, or 1-cyanocyclopropyl;- Morpholino, 3-methyl-morpholino, 3 (R) -methyl-morpholino, 3 (S) -methyl-morpholino, 3, 3-dimethylmorpho;- tetrahydro-2H-pyran-4-yl, tetrahydro-2H-pyran-3-yl, (R) -tetrahydro-2H-pyran-3-yl, (S) -tetrahydro-2H-pyran-3-yl, 2, 2, 6, 6-tetramethyltetrahydro-2H-pyran-4-yl;- 3-methoxypyrrolidin-1-yl, 3 (R) -methoxypyrrolidin-1-yl, 3 (S) -methoxypyrrolidin-1-yl, 3-hydroxy-3-methylpyrrolidin-1-yl, 3- (2-hydroxyethoxy) pyrrolidin-1-yl, 3- (trifluoromethoxy) pyrrolidin-1-yl, 3 (R) - (trifluoromethoxy) pyrrolidin-1-yl, 3 (S) - (trifluoromethoxy) pyrrolidin-1-yl, 2- (aminocarbonyl) pyrrolidin-1-yl, 2 (R) - (aminocarbonyl) pyrrolidin-1-yl, 2 (S) - (aminocarbonyl) pyrrolidin-1-yl, 3- (methoxymethyl) pyrrolidin-1-yl, 3 (R) - (methoxymethyl) pyrrolidin-1-yl, 3 (S) - (methoxymethyl) pyrrolidin-1-yl, 3-cyano-4-hydroxypyrrolidin-1-yl, cis-3-cyano-4-hydroxypyrrolidin-1-yl, trans-3-cyano-4-hydroxypyrrolidin-1-yl, 3-cyano-4-methoxypyrrolidin-1-yl, cis-3-cyano-4-methoxypyrrolidin-1-yl, trans-3-cyano-4-methoxypyrrolidin-1-yl, 2- (methoxymethyl) pyrrolidin-1-yl, 2 (R) - (methoxymethyl) pyrrolidin-1-yl, 2 (S) - (methoxymethyl) pyrrolidin-1-yl, 3-methylpyrrolidin-1-yl, 3 (R) -methylpyrrolidin-1-yl, 3 (S) -methylpyrrolidin-1-yl, pyrrolidin-1-yl, 3- (cyanomethoxy) pyrrolidin-1-yl;- 5-azaspiro [2.4] heptan-5-yl;- tetrahydrofuran-3-yl;- 3-methoxyazetidin-1-yl, 3-hydroxy-3-methylazetidin-1-yl;- 1, 4-dioxan-2-yl;- 4-aminotetrahydro-2H-pyran-4-yl, 4- (aminomethyl) tetrahydro-2H-pyran-4-yl,- 4-methoxypiperidin-1-yl, 4-hydroxy-4-methylpiperidin-1-yl, 1- (2, 2, 2-trifluoroethyl) piperidin-4-yl, 3-methoxypiperidin-1-yl, 3 (R) -methoxypiperidin-1-yl, 3 (S) -methoxypiperidin-1-yl, 3-ethoxypiperidin-1-yl, 3 (R) -ethoxypiperidin-1-yl, 3 (S) -ethoxypiperidin-1-yl;- 3-cyano-2-azabicyclo [3.1.0] hexan-2-yl, (3R) -3-cyano-2-azabicyclo [3.1.0] hexan-2-yl, (3S) -3-cyano-2-azabicyclo [3.1.0] hexan-2-yl, 3-azabicyclo [3.1.0] hexan-3-yl; 4-methylpyridin-3-yl, 5-methylpyridazin-4-yl, 5-methoxypyridazin-4-yl, 3, 5-dimethylisoxazol-4-yl, 4-methoxypyridin-3-yl, 4- (2-hydroxypropan-2-yl) pyridin-3-yl, 6-cyanopyridin-3-yl, 4-cyanopyridin-3-yl, 2-cyanopyridin-3-yl, 3-methylpyrazin-2-yl, 5-cyanopyridazin-4-yl, 5-fluoropyridazin-4-yl, 4-fluoropyridin-3-yl, 4-isopropylpyridin-3-yl, 4- (1-hydroxyethyl) pyridin-3-yl, 4- (1-methoxyethyl) pyridin-3-yl, pyridin-2-yl, or thiazol-4-yl.
- The compound of any one of claims 1-3, wherein (R 1 and R 2) , or (R 2 and R 3) , or (R 3 and R 4) , together with the atoms to which they are attached, form a fused 5-to 7-membered ring system, said fused ring system comprises 0-2 oxygen heteroatoms as ring member (s) and is optionally and independently substituted with halogen, -C 1-6alkyl, -C 1-6alkoxy, -haloC 1-6alkyl, -haloC 1-6alkoxy, or -C 3-6cycloalkyl.
- The compound of any one of claims 1-3 , wherein R 1 and R 2, together with the atoms to which they are attached, form a fused ring system selected from or R 2 and R 3, together with the atoms to which they are attached, form a fused ring system R 3 and R 4, together with the atoms to which they are attached, form a fused ring system selected from and wherein each of fused ring system is optionally and independently substituted with halogen, -C 1-6alkyl, -C 1-6alkoxy, -haloC 1-6alkyl, -haloC 1-6alkoxy, or -C 3-6cycloalkyl.
- The compound of any one of claims 1-13, wherein L is a bond.
- The compound of any one of claims 1-13, wherein Cy 1 isa. a 5-to 7-membered monocyclic heterocyclyl or heteroaryl comprising 1, 2, 3 or 4 heteroatoms selected from oxygen, nitrogen or sulfur as ring member (s) , orb. 7-to 14-membered bicyclic or tricyclic heterocyclyl or heteroaryl having 1, 2, or 3 heteroatoms selected from oxygen, nitrogen or sulfur as ring member (s) ,each of which is optionally substituted with at least one substituent R i.
- The compound of claim 15, wherein Cy 1 isa. said 5-to 7-membered monocyclic heteroaryl comprising 1, 2, 3 or 4 heteroatom (s) selected from oxygen (O) , nitrogen (N) or sulfur (S) as ring member (s) , preferably pyrazolyl, triazolyl, imidazolyl, thiazolyl, oxazolyl, furanyl, pyridinyl, pyridazinyl, pyrazinyl or pyrimidinyl, said monocyclic heteroaryl is optionally substituted with one or two substituents selected fromi. halogen;ii. cyano;iii. -C 1-6alkyl optionally substituted with halogen, hydroxy, -C 1-6alkoxy, -C (O) R m (preferably R m is morpholinyl) , or -NR mR n;iv. heterocyclyl optionally substituted with halogen, C 1-6alkyl-, -C 1-6alkyl substituted with -C 1-6alkoxy, or oxo; preferably said heterocyclyl is selected from tetrahydrofuranyl (preferably tetrahydrofuran-3-yl) , morpholinyl (preferably morpholino) , 2-oxa-5-azabicyclo [2.2.1] heptanyl (preferably 2-oxa-5-azabicyclo [2.2.1] heptan-2-yl) , 8-oxa-3-azabicyclo [3.2.1] octanyl (preferably 8-oxa-3-azabicyclo [3.2.1] octan-8-yl) , isoindolinyl (preferably isoindolin-2-yl) , each of which is optionally substituted with methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, n-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, or oxo;v. -C 3-6cycloalkyl optionally substituted with halogen, -oxo, -C 1-6alkyl, C 1-6alkoxy-, or -C 1-6alkyl substituted with -C 1-6alkoxy; orvi. -OR j, wherein R j is -C 1-6alkyl, -C 1-6alkyl substituted with -C 1-6alkoxy, or heterocyclyl;vii. oxo;b. said 7-to 14-membered bicyclic or tricyclic heteroaryl comprising 1, 2, or 3 heteroatom (s) selected from oxygen, nitrogen or sulfur as ring member (s) , preferably benzoimidazolyl, imidazopyrimidinyl, pyrazolopyrazinyl, pyrazolopyrimidinyl, benzothiophenyl, benzothiazolyl, benzoisoxazolyl, benzooxazolyl, benzoisothiazolyl, imidazopyridazinyl, imidazopyridazinyl; dihydro-4H-furo [3, 2-c] pyranyl, 6, 7-dihydro-4H-thieno [3, 2-c] pyranyl, 2, 3-dihydropyrazolo [5, 1-b] oxazolyl, 4, 5, 6, 7-tetrahydrofuro [3, 2-c] pyridinyl, 1, 3a, 4, 6, 7, 7a-hexahydropyrano [4, 3-c] pyrazolyl, 4, 5, 6, 7-tetrahydropyrazolo [1, 5-a] pyrazinyl, 4, 5, 6, 7-tetrahydropyrazolo [1, 5-a] pyrimidinyl, 4, 5, 6, 7-tetrahydropyrazolo [1, 5-a] pyrazinyl, 4, 5, 6, 7-tetrahydrothiazolo [5, 4-c] pyridinyl, 4, 5, 6, 7-tetrahydropyrazolo [1, 5-a] pyrazinyl, 6, 7-dihydro-4H-pyrazolo [5, 1-c] [1, 4] oxazinyl, 2, 3-dihydropyrazolo [5, 1-b] oxazolyl, 2, 3-dihydropyrazolo [5, 1-b] oxazolyl, 1, 3a, 4, 6, 7, 7a-hexahydropyrano [4, 3-c] pyrazolyl, 6, 7-dihydro-4H-pyrano [4, 3-d] thiazolyl, [1, 3] dioxolo [4, 5-c] pyridinyl, 2, 3-dihydro- [1, 4] dioxino [2, 3-c] pyridinyl, 3, 4-dihydro-2H-pyrido [3, 2-b] [1, 4] oxazinyl, 2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridinyl, 2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl, 3, 4-dihydro-2H-pyrido [4, 3-b] [1, 4] oxazinyl, or 2H-pyrido [3, 2-b] [1, 4] oxazin-4 (3H) -yl, each of which is optionally substituted with halogen, -C 1-6alkyl, -NH 2, or -C (O) R m, wherein R m is C 1-6alkyl; any of the said alkyl is optionally enriched in deuterium.
- The compound of claim 15, wherein Cy 1 is a 7-to 14-membered bicyclic heteroaryl which is a pyridinyl, pyrazolyl, thienyl, or thiazolyl ring fused with a 5-or 6-membered heterocyclyl ring, wherein said 5-or 6-membered heterocyclyl ring comprising one or two heteroatoms selected from oxygen or nitrogen as ring member (s) and said 5-or 6-membered heterocyclyl ring is optionally substituted with one or two C 1-6alkyl or oxo, preferably two C 1-6alkyl, more preferably two methyl, most preferably two methyl on the same carbon atom; any of the said alkyl or alkoxy is optionally enriched in deuterium.
- A compound according to any one of claims 1-18, wherein the compound is selected from:N- (4- ( (3- (methylsulfonyl) phenyl) amino) -5- (pyridazin-3-yl) pyridin-2-yl) acetamide;N- [4- [ (3-methanesulfonylphenyl) amino] -5- (oxolan-2-yl) pyridin-2-yl] acetamide;N- (5- (1H-imidazol-4-yl) -4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (5-methylpyrazin-2-yl) -4- ( (3- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (4- ( (3- (methylsulfonyl) phenyl) amino) -5- (pyrazin-2-yl) pyridin-2-yl) acetamide;N- (5- (2, 6-dimethylpyrimidin-4-yl) -4- ( (3- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (4- ( (3- (methylsulfonyl) phenyl) amino) -5- (2-oxopyrrolidin-1-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-4-yl) -4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (furan-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-1, 2, 4-triazol-3-yl) -4- ( (3- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (4- ( (3-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-4-yl) pyridin-2-yl) acetamide;N- (4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1H-pyrazol-1-yl) pyridin-2-yl) acetamide;N- (4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1- (2-morpholino-2-oxoethyl) -1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1- (2-hydroxyethyl) -1H-pyrazol-3-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1- (2-methoxyethyl) -1H-pyrazol-3-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (6-cyano-4'- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5-cyano-4'- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (1H-imidazol-1-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-cyclobutyl-1H-pyrazol-3-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2-aminopropan-2-yl) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (1H-imidazol-4-yl) -4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1H-imidazol-4-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1H-imidazol-4-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) -5- (pyridazin-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (cyclopropylmethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (6-methoxypyridazin-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (6-methoxypyridazin-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- ( (2S, 6R) -2, 6-dimethylmorpholino) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (6-methoxypyridazin-3-yl) pyridin-2-yl) acetamide;N- (5- (6-methoxypyridazin-3-yl) -4- ( (6- (methylsulfonyl) - [1, 3] dioxolo [4, 5-c] pyridin-4-yl) amino) pyridin-2-yl) acetamide;N- (5- (6-isopropoxypyridazin-3-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (6-isopropoxypyridazin-3-yl) -4- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (6-isopropoxypyridazin-3-yl) -4- (4- (methoxy-d3) -6- (methylsulfonyl) pyridin-2-ylamino) pyridin-2-yl) acetamide;N- (4'- ( (3- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) - [3, 3'-bipyridin] -6-yl) acetamide;N- (4'- (phenylamino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (6-sulfamoylpyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (2-hydroxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4- (methoxymethyl) -4'- ( (6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4- (2-hydroxypropan-2-yl) -4'- ( (3- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4- (2-hydroxypropan-2-yl) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (methylsulfonyl) phenyl) amino) -5-morpholino- [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 2-dimethylmorpholino) -4'- ( (6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3-methoxyphenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (2- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-oxa-5-azabicyclo [2.2.1] heptan-5-yl) -4'- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4-chloro-5- (2-hydroxypropan-2-yl) -4'- ( (6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2- (methoxymethyl) morpholino) - [2, 3'-bipyridin] -6'-yl) acetamide;N4'- (3- (methylsulfonyl) phenyl) - [2, 3'-bipyridine] -4', 6'-diamine;N- (4'- ( (3- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) cyclopropanecarboxamide;(S) -N- (4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) -5- ( (tetrahydrofuran-3-yl) oxy) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (2-hydroxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- ( (tetrahydrofuran-3-yl) oxy) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (6- (methylsulfonyl) pyridin-2-yl) amino) -5- ( (tetrahydrofuran-3-yl) oxy) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (8-oxa-3-azabicyclo [3.2.1] octan-3-yl) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 5-dimethylmorpholino) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamid;N- (5- (cis-2, 6-dimethylmorpholino) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (3- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (cyclopropylmethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- ( (cis) -2, 6-dimethylmorpholino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (cyclopropylmethoxy) -5- (methylsulfonyl) phenyl) amino) -5- ( (cis) -2, 6-dimethylmorpholino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (trans) -2, 6-dimethylmorpholino) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (Cis-2, 6-dimethylmorpholino) -4'- ( (7- (methylsulfonyl) -2, 3-dihydro- [1, 4] dioxino [2, 3-c] pyridin-5-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (4-ethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (4- ( (R) -2-hydroxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- ( (R) -sec-butoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- ( (cis) -2, 6-dimethylmorpholino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (3-methoxy-5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (3-fluoro-5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3-cyano-5- (methylsulfonyl) phenyl) amino) -5- ( (cis) -2, 6-dimethylmorpholino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (cis-2, 6-dimethylmorpholino) -4'- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (4- (methoxy-d3) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (cis-2, 6-dimethylmorpholino) -4'- ( (4- (1-methoxyethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (4- ( (R or S) -1-methoxyethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- ( (cis) -2, 6-dimethylmorpholino) -4'- ( (4- ( (R or S) -1-methoxyethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (cis-2, 6-dimethylmorpholino) -4'- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (cis-2, 6-dimethylmorpholino) -4'- ( (6- (methylsulfonyl) pyrazin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (cis-2, 6-dimethylmorpholino) -4'- ( (4- ( (S) -3-methylmorpholino) -6- (methylsulfon-yl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) ace-tamide.;N- (5- (cis-2, 6-dimethylmorpholino) -4'- ( (4- ( (R) -3-methylmorpholino) -6- (methylsulfon-yl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) ace-tamide.;N- (5- (cis-2, 6-dimethyl morpholino) -4'- ( (4- (3-methoxy azetidin-1-yl) -6- (methylsulfonyl) pyridin -2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-methoxyethoxy) -4'- ( (6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-methoxyethoxy) -4'- ( (3- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-methoxyethoxy) -4'- ( (3- (methylsulfonyl) -5- (trifluoromethyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-methoxyethoxy) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-methoxyethoxy) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-methoxyethoxy) - [2, 3'-bipyridin] -6'-yl) acetamide;(R) -N- (5- (2-methoxyethoxy) -4'- ( (4- (2-methoxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-methoxyethoxy) -4'- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-ethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-methoxyethoxy) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (cyclopropylmethoxy) -5- (methylsulfonyl) phenyl) amino) -5- (2-methoxyethoxy) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (cyclopropylmethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-methoxyethoxy) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (methoxymethyl) -4'- ( (3- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (methoxymethyl) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;(R) -N- (5- (methoxymethyl) -4'- ( (4- (2-methoxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (methoxymethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (methoxymethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (2-hydroxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (methoxymethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (methoxymethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- ( (1r, 3r) -3-hydroxycyclobutoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (methoxymethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (methoxymethyl) -4'- ( (4- (methoxymethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (methylsulfonyl) phenyl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3-methyl-5- (methylsulfonyl) phenyl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3-cyano-5- (methylsulfonyl) phenyl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- ( (trans) -3-hydroxycyclobutoxy) -5- (methylsulfonyl) phenyl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (cyclopropylmethoxy) -5- (methylsulfonyl) phenyl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (2-hydroxyethoxy) -5- (methylsulfonyl) phenyl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (2-methoxyethoxy) -5- (methylsulfonyl) phenyl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-ethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamidecarboxamide;N- (4'- ( (4- (2-hydroxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5-fluoro-4'- ( (3- (methylsulfonyl) -5- (trifluoromethyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5-fluoro-4'- ( (3-isopropoxy-5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5-fluoro-4'- ( (3- ( (trans) -3-hydroxycyclobutoxy) -5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5-fluoro-4'- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5-fluoro-4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5-fluoro-4'- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-ethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5-fluoro- [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;(S) -N- (4'- ( (4- (2-hydroxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (trifluoromethyl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5-fluoro-4'- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3, 4-dimethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5-fluoro- [2, 3'-bipyridin] -6'-yl) acetamide;N- (5-fluoro-4'- ( (4- (methoxy-d3) -6- (methylsulfonyl) pyridine-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-cyclopropyl-6- (methylsulfonyl) pyridin-2-yl) amino) -5-fluoro- [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (methylsulfonyl) phenyl) amino) -5- (3-oxomorpholino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (6- (methylsulfonyl) pyridin-2-yl) amino) -5- (3-oxomorpholino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (2-hydroxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (3-oxomorpholino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (3-oxomorpholino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide.;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3- (methylsulfonyl) -5- (trifluoro methyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3-methoxy-5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (4- (2-methoxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (2-hydroxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (trans) -3-hydroxycyclobutoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (6- (methylsulfonyl) -4- (oxetan-3-ylmethoxy) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (4- (methoxymethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-cyano-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3- (2-methoxyethoxy) -5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3- (methoxymethyl) -5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3- (3-hydroxypyrrolidin-1-yl) -5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3- (methylsulfonyl) -5- (trifluoromethoxy) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3-fluoro-5- (methylsulfonyl) phenyl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3-cyano-5- (methylsulfonyl) phenyl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3-methyl-5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (cyclopropylmethoxy) -5- (methylsulfonyl) phenyl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3-cyclopropoxy-5- (methylsulfonyl) phenyl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3-isopropoxy-5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (3- (difluoromethyl) -5- (methylsulfonyl) phenyl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (4- (2-hydroxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (6- (methylsulfonyl) -4- (oxetan-3-yloxy) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (cis-3-hydroxycyclobutoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (4- (3-methoxycyclobutoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4- (cyclopropylmethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-cyclobutoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (4-ethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (5-fluoro-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (2-methyl-5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4'- ( (6- (ethylsulfonyl) -4-isopropoxypyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (7- (methylsulfonyl) -2, 3-dihydro- [1, 4] dioxino [2, 3-c] pyridin-5-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;(R) -N- (5- (2-hydroxypropan-2-yl) -4'- ( (4- (2-hydroxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (4-isobutoxy-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;(S) -N- (4'- ( (4- (sec-butoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;(R) -N- (4'- ( (4- (sec-butoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2-hydroxypropan-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4'- ( (3-isopropoxy-5- (methylsulfonyl) phenyl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (cyclopropylmethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6-sulfamoylpyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (6- (ethylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (3- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (4- ( (3-cyano-5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (3-methyl-5- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (4- ( (3-methoxy-5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (3- (methylsulfonyl) -5- (trifluoromethoxy) phenyl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2-methoxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;(R) -N- (4- ( (4- (2-methoxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2-hydroxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- ( (trans) -3-hydroxycyclobutoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- ( (cis) -3-hydroxycyclobutoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (3-methoxycyclobutoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (methoxymethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (cyanomethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) -4- (oxetan-3-yloxy) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (3-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2-hydroxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) -4- (oxetan-3-ylmethoxy) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4-cyano-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (3-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (6- (cyclopropylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (6- (isopropylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3-fluoro-5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3-chloro-5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3- (difluoromethyl) -5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (3- (methylsulfonyl) -5- (trifluoromethyl) phenyl) amino) pyridin-2-yl) acetamide;N- (4- ( (3- (methoxymethyl) -5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3- (2-methoxyethoxy) -5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3-cyclopropoxy-5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3- ( (trans) -3-hydroxycyclobutoxy) -5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) -4-phenylpyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) -4-phenoxypyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4-chloro-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (1-methoxyethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (difluoromethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4-ethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4-cyclobutoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (cyclopentyloxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) -4- ( (tetrahydrofuran-3-yl) oxy) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (4- ( (4- (2-hydroxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2, 3-dihydroxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (5-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (5-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) -4- (trifluoromethyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (6- (ethylsulfonyl) -4-isopropoxypyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (5-fluoro-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;(S) -N- (4- ( (3- (2-hydroxypropoxy) -5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3- (2-hydroxyethoxy) -5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;(R) -N- (4- ( (3- (2-hydroxypropoxy) -5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (difluoromethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4-isobutoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;(S) -N- (4- ( (4- (sec-butoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (3- (difluoromethoxy) -5- (methylsulfonyl) phenyl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3- (difluoromethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (7- (methylsulfonyl) -2, 3-dihydro- [1, 4] dioxino [2, 3-c] pyridin-5-yl) amino) pyridin-2-yl) acetamide;(R) -N- (4- ( (4- (sec-butoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-cyclopropyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-cyclopropyl-1H-pyrazol-3-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-cyclopropyl-1H-pyrazol-3-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-cyclopropyl-1H-pyrazol-3-yl) -4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (4- (methoxymethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (3- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (3-methoxy-5- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (4- ( (3-cyano-5- (methylsulfonyl) phenyl) amino) -5- (1-ethyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (3-methyl-5- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (3- (methoxymethyl) -5- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (3- (methylsulfonyl) -5- (trifluoromethyl) phenyl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (3- (2-methoxyethoxy) -5- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (3- (2-hydroxyethoxy) -5- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (4- ( (3- (cyclopropylmethoxy) -5- (methylsulfonyl) phenyl) amino) -5- (1-ethyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (cyclopentyloxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-ethyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4-ethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-ethyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (4- (2-hydroxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-ethyl-1H-pyrazol-3-yl) -4- ( (3-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-isopropyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-isopropyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-isopropyl-1H-pyrazol-3-yl) -4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-isopropyl-1H-pyrazol-3-yl) -4- ( (3- (methylsulfonyl) -5- (trifluoromethyl) phenyl) amino) pyridin-2-yl) acetamide;N- (4- ( (3-isopropoxy-5- (methylsulfonyl) phenyl) amino) -5- (1-isopropyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-isopropyl-1H-pyrazol-3-yl) -4- ( (3-methoxy-5- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (2-hydroxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-isopropyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3- (2-hydroxyethoxy) -5- (methylsulfonyl) phenyl) amino) -5- (1-isopropyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (3- (methylsulfonyl) phenyl) amino) -5- (1- (tetrahydrofuran-3-yl) -1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1- (tetrahydrofuran-3-yl) -1H-pyrazol-3-yl) pyridin-2-yl) acetamide;(R) -N- (4- ( (3- (methylsulfonyl) -5- (trifluoromethyl) phenyl) amino) -5- (1- (tetrahydrofuran-3-yl) -1H-pyrazol-3-yl) pyridin-2-yl) acetamide;(S) -N- (4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1- (tetrahydrofuran-3-yl) -1H-pyrazol-3-yl) pyridin-2-yl) acetamide;(R) -N- (4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1- (tetrahydrofuran-3-yl) -1H-pyrazol-3-yl) pyridin-2-yl) acetamide;(R) -N- (4- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1- (tetrahydrofuran-3-yl) -1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1, 5-dimethyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1, 5-dimethyl-1H-pyrazol-3-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1, 5-dimethyl-1H-pyrazol-3-yl) -4- ( (3- (2-hydroxyethoxy) -5- (methylsulfonyl) phenyl) amino) pyridin-2-yl) acetamide;N- (5- (1, 5-dimethyl-1H-pyrazol-3-yl) -4- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1, 5-dimethyl-1H-pyrazol-3-yl) -4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (1, 5-dimethyl-1H-pyrazol-3-yl) -4- ( (4- (2-methoxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1, 5-dimethyl-1H-pyrazol-3-yl) -4- ( (4-ethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-5-morpholino-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-5-morpholino-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2-hydroxypropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-5-morpholino-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridine-2-yl) amino) pyridin-2-yl) acetamide;N- (5- ( [1, 3] dioxolo [4, 5-b] pyridin-5-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (3, 4-dihydro-2H-pyrido [4, 3-b] [1, 4] oxazin-7-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (imidazo [1, 2-b] pyridazin-6-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (6, 7-dihydro-4H-pyrazolo [5, 1-c] [1, 4] oxazin-2-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (4-acetyl-3, 4-dihydro-2H-pyrido [3, 2-b] [1, 4] oxazin-6-yl) -4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 3-dihydro- [1, 4] dioxino [2, 3-c] pyridin-7-yl) -4- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (benzo [b] thiophen-2-yl) -4- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (6, 7-dihydro-4H-thieno [3, 2-c] pyran-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 3-dihydro- [1, 4] dioxino [2, 3-c] pyridin-7-yl) -4- ( (4-ethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 3-dihydro- [1, 4] dioxino [2, 3-c] pyridin-7-yl) -4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- ( [1, 3] dioxolo [4, 5-b] pyridin-5-yl) -4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- ( [1, 3] dioxolo [4, 5-b] pyridin-5-yl) -4- ( (4-ethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- ( [1, 3] dioxolo [4, 5-b] pyridin-5-yl) -4- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (cyclopropylmethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (5-methyl-4, 5, 6, 7-tetrahydrothiazolo [5, 4-c] pyridin-2-yl) pyridin-2-yl) acetamide;N- (5- (2, 3-dihydro- [1, 4] dioxino [2, 3-c] pyridin-7-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 3-dihydro- [1, 4] dioxino [2, 3-c] pyridin-7-yl) -4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (6, 7-dihydro-4H-pyrazolo [5, 1-c] [1, 4] oxazin-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- ( (1, 4-dioxan-2-yl) methoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridine-6-yl) -4- ( (6- (methylsulfonyl) pyrazin-2-yl) amino) pyridine-2-yl) acetamide;N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] yridine-6-yl) -4- ( (4- (2-hydroxypropan-2-yl) -6- (methylsulfonyl) pyridine-2-yl) amino) pyridine-2-yl) acetamide;N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridine-6-yl) -4- ( (5-fluoro-4-methyl-6- (methylsulfonyl) pyridine-2-yl) amino) pyridine-2-yl) acetamide;N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4-morpholinopyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4-morpholinopyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (methoxy-d3) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (3, 4-dimethoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methyl-morpholino) -6- (methylsulfonyl) pyridin-2-yl) amino) -pyridin-2-yl) acetamide.;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methyl-morpholino) -6- (methylsulfonyl) pyridin-2-yl) amino) -pyridin-2-yl) acetamide.;N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (methoxy-d3) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-methoxy-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methylmorpholino) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methylmorpholino) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (1-methoxyethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (3, 3-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (1-methoxyethyl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methoxypyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methoxypyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide.;N- (4- ( (4- (4-aminotetrahydro-2H-pyran-4-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (4- (aminomethyl) tetrahydro-2H-pyran-4-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methoxyazetidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R/S) -N- (4- ( (4- (1, 4-dioxan-2-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;(S/R) -N- (4- ( (4- (1, 4-dioxan-2-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (4-methoxypiperidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- ( (cis) -3-methoxycyclobutyl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamid;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- ( (trans) -3-methoxycyclobutyl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (4-hydroxy-4-methylpiperidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-hydroxy-3-methylazetidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyrid-in-2-yl) acetamide ;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-hydroxy-3-methylpyrrolidin-1-yl) -6- (methyl sulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (6- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -5- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) pyridazin-3-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3- (2-hydroxyethoxy) pyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (1- (2, 2, 2-trifluoroethyl) piperidin-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3- (2-hydroxyethoxy) pyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-methyl-6'- (methylsulfonyl) - [3, 4'-bipyridin] -2'-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4-cyano-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-methyl-6- (methylsulfonyl) -3-oxo-3, 4-dihydropyrazin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methoxypiperidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methoxypiperidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-ethoxypiperidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-ethoxypiperidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (3- (trifluoromethoxy) pyrrolidin-1-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (3- (trifluoromethoxy) pyrrolidin-1-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -1- (2- ( (2-acetamido-5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-4-yl) amino) -6- (methylsulfonyl) pyridin-4-yl) pyrrolidine-2-carboxamide;(R) -1- (2- ( (2-acetamido-5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-4-yl) amino) -6- (methylsulfonyl) pyridin-4-yl) pyrrolidine-2-carboxamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3- (methoxymethyl) pyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3- (methoxymethyl) pyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-3-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-3-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (5- (3-methoxypyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (5- (3-methoxypyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -5- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (5-methylpyridazin-4-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (5-methoxypyridazin-4-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (cis-3-cyano-4-hydroxypyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (trans-3-cyano-4-hydroxypyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (cis-3-cyano-4-methoxypyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (trans-3-cyano-4-methoxypyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydrofuran-3-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydrofuran-3-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (2- (methoxymethyl) pyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (2- (methoxymethyl) pyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -3- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (3- (3-methoxypyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (3- (3-methoxypyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;cis-N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- ( (cis-4-hydroxycyclohexyl) oxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- ( (trans-4-hydroxycyclohexyl) oxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- ( (cis-4-methoxycyclohexyl) oxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- ( (trans-4-methoxycyclohexyl) oxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (5-azaspiro [2.4] heptan-5-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- ( (3-methyloxetan-3-yl) methoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3, 5-dimethylisoxazol-4-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- ( (2, 4-dioxothiazolidin-3-yl) methyl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-methoxy-6'- (methylsulfonyl) - [3, 4'-bipyridin] -2'-yl) amino) pyridin-2-yl) acetamide;(R) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methylpyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(S) -N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methylpyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (pyrrolidin-1-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (2-hydroxypropan-2-yl) -6'- (methylsulfonyl) - [3, 4'-bipyridin] -2'-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (3-azabicyclo [3.1.0] hexan-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;(S) -N- (4- ( (4- (3- (cyanomethoxy) pyrrolidin-1-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (6-cyano-6'- (methylsulfonyl) - [3, 4'-bipyridin] -2'-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (2-cyano-6'- (methylsulfonyl) - [3, 4'-bipyridin] -2'-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3-methylpyrazin-2-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (2, 2, 6, 6-tetramethyltetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;(R) -N- (4- ( (4- (2, 2-dichlorocyclopropyl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;(S) -N- (4- ( (4- (2, 2-dichlorocyclopropyl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (5-cyanopyridazin-4-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (4-cyano-6'- (methylsulfonyl) - [3, 4'-bipyridin] -2'-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (5-fluoropyridazin-4-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-fluoro-6'- (methylsulfonyl) - [3, 4'-bipyridin] -2'-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6'- (methylsulfonyl) - [2, 4'-bipyridin] -2'-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (thiazol-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (1-cyanocyclopropyl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (4- ( (3R) -3-cyano-2-azabicyclo [3.1.0] hexan-2-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (4- ( (3S) -3-cyano-2-azabicyclo [3.1.0] hexan-2-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (2-methyl-2-morpholinopropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (2-methoxy-2-methylpropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (2-hydroxy-2-methylpropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (3, 3-dimethylmorpholino) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4-isopropyl-6'- (methylsulfonyl) - [3, 4'-bipyridin] -2'-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (1-hydroxyethyl) -6'- (methylsulfonyl) - [3, 4'-bipyridin] -2'-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (1-methoxyethyl) -6'- (methylsulfonyl) - [3, 4'-bipyridin] -2'-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) - [1, 3] dioxolo [4, 5-c] pyridin-4-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (7- (methylsulfonyl) -2, 3-dihydro- [1, 4] dioxino [2, 3-c] pyridin-5-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (trifluoromethyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (difluoromethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (4- ( (4-cyclobutoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (2, 2-dimethyl-2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) pyridin-2-yl) acetamide;N- (5- (2, 2-bis (methyl-d3) -2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-bis (methyl-d3) -2, 3-dihydro- [1, 4] dioxino [2, 3-b] pyridin-6-yl) -4- ( (4- (methoxy-d3) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (4, 4-dimethyl-4, 5-dihydrothiazol-2-yl) -4- ( (6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (4, 4-dimethyl-4, 5-dihydrothiazol-2-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1, 3a, 4, 6, 7, 7a-hexahydropyrano [4, 3-c] pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (6, 7-dihydro-4H-pyrano [4, 3-d] thiazol-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4-isopropoxy-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (5-methyl-4, 5, 6, 7-tetrahydropyrazolo [1, 5-a] pyrazin-2-yl) pyridin-2-yl) acetamide;N- (5- ( [1, 3] dioxolo [4, 5-c] pyridin-6-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- ( [1, 3] dioxolo [4, 5-c] pyridin-4-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (benzo [d] [1, 3] dioxol-4-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (5-methyl-4, 5, 6, 7-tetrahydrothiazolo [5, 4-c] pyridin-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (imidazo [1, 2-a] pyrimidin-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-1, 4-dihydrochromeno [4, 3-c] pyrazol-6-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (imidazo [2', 1': 2, 3] thiazolo [5, 4-b] pyridin-7-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-1, 4-dihydropyrazolo [3', 4': 4, 5] pyrano [2, 3-b] pyridin-7-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4'- ( (4, 4-dioxido-2, 3-dihydro- [1, 4] oxathiino [3, 2-b] pyridin-6-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (4- ( (4, 4-dioxido-2, 3-dihydro- [1, 4] oxathiino [3, 2-b] pyridin-6-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (imidazo [1, 2-b] pyridazin-6-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (7- (methylsulfonyl) -3, 4-dihydro-2H-pyrano [3, 2-c] pyridin-5-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (5, 5-dioxido-3, 4-dihydro-2H- [1, 4] oxathiepino [3, 2-b] pyridin-7-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2-hydroxypropan-2-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydrofuran-3-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (1-hydroxycyclopropyl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2-hydroxy-2-methylpropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (3-hydroxy-2, 2-dimethylpropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (imidazo [1, 5-b] pyridazin-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (3-hydroxytetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (4- (1-methyl-1H-pyrazol-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- ( (1-hydroxycyclopropyl) methoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- ( (1-methoxycyclopropyl) methoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) -4-morpholinopyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (benzo [d] thiazol-2-yl) -4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (1, 1-dioxido-3, 4-dihydro-2H-thiopyrano [2, 3-b] pyridin-7-yl) amino) -5- (1-methyl-1H-pyrazol-3-yl) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (7- (methylsulfonyl) -3, 4-dihydro-2H-pyrano [3, 2-c] pyridin-5-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) - [1, 3] dioxolo [4, 5-c] pyridin-4-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (6- (methylsulfonyl) imidazo [1, 2-a] pyrazin-8-yl) amino) pyridin-2-yl) acetamide;N- (5- (1-methyl-1H-pyrazol-3-yl) -4- ( (5- (methylsulfonyl) -3, 4-dihydro-2H-pyrano [3, 2-c] pyridin-7-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (4- (2-hydroxypropan-2-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (6- (methylsulfonyl) -4- (tetrahydrofuran-3-yl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (4- (1-hydroxycyclopropyl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (4- (2-hydroxy-2-methylpropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (4- (3-hydroxy-2, 2-dimethylpropoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (4- (3-methoxytetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (4- (3-hydroxytetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (4- (1-methyl-1H-pyrazol-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (4- ( (1-hydroxycyclopropyl) methoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (4- ( (1-methoxycyclopropyl) methoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (6- (methylsulfonyl) -4-morpholinopyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (5, 5-dioxido-3, 4-dihydro-2H- [1, 4] oxathiepino [3, 2-b] pyridin-7-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (1, 1-dioxido-3, 4-dihydro-2H-thiopyrano [2, 3-b] pyridin-7-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (7- (methylsulfonyl) -3, 4-dihydro-2H-pyrano [3, 2-c] pyridin-5-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (6- (methylsulfonyl) - [1, 3] dioxolo [4, 5-c] pyridin-4-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (6- (methylsulfonyl) imidazo [1, 2-a] pyrazin-8-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (5- (methylsulfonyl) -3, 4-dihydro-2H-pyrano [3, 2-c] pyridin-7-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (6, 7-dihydro-4H-pyrano [4, 3-d] thiazol-2-yl) -4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (benzo [d] [1, 3] dioxol-4-yl) -4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (benzo [d] isoxazol-3-yl) -4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (benzo [d] isothiazol-3-yl) -4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (benzo [b] thiophen-2-yl) -4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (imidazo [1, 2-a] pyrimidin-2-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1, 4-dihydrochromeno [4, 3-c] pyrazol-6-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (imidazo [2', 1': 2, 3] thiazolo [5, 4-b] pyridin-7-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-methyl-1, 4-dihydropyrazolo [3', 4': 4, 5] pyrano [2, 3-b] pyridin-7-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (6-oxo-1, 6-dihydropyridazin-3-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (6-oxopyridazin-1 (6H) -yl) pyridin-2-yl) acetamide;N- (5- (6- ( (2S, 6R) -2, 6-dimethylmorpholino) pyridazin-3-yl) -4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (3-oxo-8, 9-dihydropyrano [4, 3, 2-de] phthalazin-2 (3H) -yl) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (7-methyl-3-oxo-8, 9-dihydro-3H-pyrido [4, 3, 2-de] phthalazin-2 (7H) -yl) pyridin-2-yl) acetamide;N- (4'- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (1-oxoisoindolin-2-yl) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 3-dihydropyrazolo [5, 1-b] oxazol-6-yl) -4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-2, 3-dihydropyrazolo [5, 1-b] oxazol-6-yl) -4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (5'H, 7'H-spiro [cyclopropane-1, 6'-pyrazolo [5, 1-b] [1, 3] oxazin] -2'-yl) pyridin-2-yl) acetamide;N- (4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (pyridin-2-yloxy) pyridin-2-yl) acetamide;N- (5- (1H-imidazol-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (4- (2-hydroxypropan-2-yl) furan-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (furan-2-yl) -4- ( (4- (3-methoxytetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (1H-benzo [d] imidazol-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (3-fluoro-5- (2-hydroxypropan-2-yl) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (3-fluoro-5- (2-hydroxypropan-2-yl) -4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2-hydroxypropan-2-yl) -4-methyl-4'- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (6- (methylsulfonyl) -4- ( (tetrahydrofuran-3-yl) methoxy) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (2, 6-dimethylmorpholino) -4'- ( (6- (methylsulfonyl) -4- ( ( (tetrahydrofuran-3-yl) oxy) methyl) pyridin-2-yl) amino) - [2, 3'-bipyridin] -6'-yl) acetamide;N- (5- (3-methoxy-1-methyl-1H-pyrazol-4-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (3-methoxy-1-methyl-1H-pyrazol-4-yl) pyridin-2-yl) acetamide;N- (5- (6, 7-dihydro-4H-furo [3, 2-c] pyran-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (5-methyl-4, 5, 6, 7-tetrahydrofuro [3, 2-c] pyridin-2-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (cyclopropylmethoxy) -4- ( (4- (1-methyl-1H-pyrazol-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- ( (1-hydroxycyclopropyl) methoxy) -4- ( (4- (1-methyl-1H-pyrazol-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (benzo [d] oxazol-2-yl) -4- ( (4- (3- (hydroxymethyl) tetrahydrofuran-3-yl) -6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (5- (2, 2-dimethyl-3-oxo-3, 4-dihydro-2H-pyrido [3, 2-b] [1, 4] oxazin-6-yl) -4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) pyridin-2-yl) acetamide;N- (4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (pyrazolo [1, 5-a] pyrazin-2-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (pyrazolo [1, 5-a] pyrazin-2-yl) pyridin-2-yl) acetamide;N- (4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (pyrazolo [1, 5-c] pyrimidin-2-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (pyrazolo [1, 5-c] pyrimidin-2-yl) pyridin-2-yl) acetamide;N- (4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (pyrazolo [1, 5-a] pyrimidin-2-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (pyrazolo [1, 5-a] pyrimidin-2-yl) pyridin-2-yl) acetamide;N- (4- ( (4-methyl-6- (methylsulfonyl) pyridin-2-yl) amino) -5- (pyrazolo [1, 5-a] pyrimidin-5-yl) pyridin-2-yl) acetamide;N- (4- ( (4- (2-methoxyethoxy) -6- (methylsulfonyl) pyridin-2-yl) amino) -5- (pyrazolo [1, 5-a] pyrimidin-5-yl) pyridin-2-yl) acetamide; orN- (5- (2, 2-dimethyl-2, 3-dihydro-1H-pyrido [2, 3-b] [1, 4] oxazin-6-yl) -4- ( (6- (methylsulfonyl) -4- (tetrahydro-2H-pyran-4-yl) pyridin-2-yl) amino) pyridin-2-yl) acetamide.
- A pharmaceutical composition comprising one or more compounds according to any one of claims 1-19 or a stereoisomer or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.
- A method of treating a disease, comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound according to any one of claims 1-19, wherein the disease is an inflammatory or autoimmune disease.
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP21829711.7A EP4168398A1 (en) | 2020-06-22 | 2021-06-21 | Tyk-2 inhibitor |
JP2022579058A JP2023531221A (en) | 2020-06-22 | 2021-06-21 | TYK-2 inhibitor |
IL299294A IL299294A (en) | 2020-06-22 | 2021-06-21 | Tyk-2 inhiitor |
AU2021294706A AU2021294706A1 (en) | 2020-06-22 | 2021-06-21 | Tyk-2 inhibitor |
CA3183368A CA3183368A1 (en) | 2020-06-22 | 2021-06-21 | Tyk-2 inhibitor |
US18/011,590 US20240043435A1 (en) | 2020-06-22 | 2021-06-21 | Tyk-2 inhibitor |
BR112022025946A BR112022025946A2 (en) | 2020-06-22 | 2021-06-21 | COMPOUND, PHARMACEUTICAL COMPOSITION AND METHOD OF TREATMENT OF A DISEASE |
KR1020237002577A KR20230042278A (en) | 2020-06-22 | 2021-06-21 | TYK-2 inhibitors |
CN202180044409.1A CN115715288A (en) | 2020-06-22 | 2021-06-21 | TYK-2 inhibitors |
MX2022015679A MX2022015679A (en) | 2020-06-22 | 2021-06-21 | Tyk-2 inhibitor. |
ZA2023/00912A ZA202300912B (en) | 2020-06-22 | 2023-01-20 | Tyk-2 inhibitor |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNPCT/CN2020/097557 | 2020-06-22 | ||
CN2020097557 | 2020-06-22 | ||
CNPCT/CN2020/119750 | 2020-09-30 | ||
CN2020119750 | 2020-09-30 | ||
CNPCT/CN2021/093815 | 2021-05-14 | ||
CN2021093815 | 2021-05-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2021259208A1 true WO2021259208A1 (en) | 2021-12-30 |
Family
ID=79281960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2021/101282 WO2021259208A1 (en) | 2020-06-22 | 2021-06-21 | Tyk-2 inhibitor |
Country Status (13)
Country | Link |
---|---|
US (1) | US20240043435A1 (en) |
EP (1) | EP4168398A1 (en) |
JP (1) | JP2023531221A (en) |
KR (1) | KR20230042278A (en) |
CN (1) | CN115715288A (en) |
AU (1) | AU2021294706A1 (en) |
BR (1) | BR112022025946A2 (en) |
CA (1) | CA3183368A1 (en) |
IL (1) | IL299294A (en) |
MX (1) | MX2022015679A (en) |
TW (1) | TW202200561A (en) |
WO (1) | WO2021259208A1 (en) |
ZA (1) | ZA202300912B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023076161A1 (en) | 2021-10-25 | 2023-05-04 | Kymera Therapeutics, Inc. | Tyk2 degraders and uses thereof |
WO2023116822A1 (en) * | 2021-12-23 | 2023-06-29 | Beigene, Ltd. | Solid forms of a tyk2 inhibitor, method of preparation, and use thereof |
WO2024015497A1 (en) * | 2022-07-14 | 2024-01-18 | Biogen Ma Inc. | Tyrosine kinase 2 inhibitors and uses thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012117059A1 (en) * | 2011-03-02 | 2012-09-07 | Lead Discovery Center Gmbh | Pharmaceutically active disubstituted pyridine derivatives |
WO2018071794A1 (en) * | 2016-10-14 | 2018-04-19 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
WO2020086616A1 (en) * | 2018-10-22 | 2020-04-30 | Fronthera U.S. Pharmaceuticals Llc | Tyk2 inhibitors and uses thereof |
-
2021
- 2021-06-21 MX MX2022015679A patent/MX2022015679A/en unknown
- 2021-06-21 WO PCT/CN2021/101282 patent/WO2021259208A1/en unknown
- 2021-06-21 KR KR1020237002577A patent/KR20230042278A/en unknown
- 2021-06-21 US US18/011,590 patent/US20240043435A1/en active Pending
- 2021-06-21 EP EP21829711.7A patent/EP4168398A1/en active Pending
- 2021-06-21 CA CA3183368A patent/CA3183368A1/en active Pending
- 2021-06-21 CN CN202180044409.1A patent/CN115715288A/en active Pending
- 2021-06-21 BR BR112022025946A patent/BR112022025946A2/en unknown
- 2021-06-21 JP JP2022579058A patent/JP2023531221A/en active Pending
- 2021-06-21 TW TW110122532A patent/TW202200561A/en unknown
- 2021-06-21 AU AU2021294706A patent/AU2021294706A1/en active Pending
- 2021-06-21 IL IL299294A patent/IL299294A/en unknown
-
2023
- 2023-01-20 ZA ZA2023/00912A patent/ZA202300912B/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012117059A1 (en) * | 2011-03-02 | 2012-09-07 | Lead Discovery Center Gmbh | Pharmaceutically active disubstituted pyridine derivatives |
WO2018071794A1 (en) * | 2016-10-14 | 2018-04-19 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
WO2020086616A1 (en) * | 2018-10-22 | 2020-04-30 | Fronthera U.S. Pharmaceuticals Llc | Tyk2 inhibitors and uses thereof |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023076161A1 (en) | 2021-10-25 | 2023-05-04 | Kymera Therapeutics, Inc. | Tyk2 degraders and uses thereof |
WO2023116822A1 (en) * | 2021-12-23 | 2023-06-29 | Beigene, Ltd. | Solid forms of a tyk2 inhibitor, method of preparation, and use thereof |
WO2024015497A1 (en) * | 2022-07-14 | 2024-01-18 | Biogen Ma Inc. | Tyrosine kinase 2 inhibitors and uses thereof |
Also Published As
Publication number | Publication date |
---|---|
TW202200561A (en) | 2022-01-01 |
MX2022015679A (en) | 2023-01-16 |
ZA202300912B (en) | 2023-09-27 |
EP4168398A1 (en) | 2023-04-26 |
IL299294A (en) | 2023-02-01 |
BR112022025946A2 (en) | 2023-01-24 |
US20240043435A1 (en) | 2024-02-08 |
JP2023531221A (en) | 2023-07-21 |
KR20230042278A (en) | 2023-03-28 |
AU2021294706A1 (en) | 2023-02-23 |
CN115715288A (en) | 2023-02-24 |
CA3183368A1 (en) | 2021-12-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20220402915A1 (en) | Bcl-2 inhibitors | |
WO2021259208A1 (en) | Tyk-2 inhibitor | |
WO2019238067A1 (en) | Pyrrolo [2, 3-b] pyridines or pyrrolo [2, 3-b] pyrazines as hpk1 inhibitor and the use thereof | |
WO2020103896A1 (en) | Pyrrolo[2,3-b]pyridines as hpk1 inhibitor and uses thereof | |
WO2021013083A1 (en) | Tricyclic compounds as hpk1 inhibitor and the use thereof | |
WO2019223632A1 (en) | Heterocyclic compounds as kinase inhibitors, compositions comprising the heterocyclic compound, and methods of use thereof | |
AU2020299892A1 (en) | Pyrrolo [2, 3-b] pyrazines as HPK1 inhibitor and the use thereof | |
WO2021032148A1 (en) | Aminopyrazine compounds as hpk1 inhibitor and the use thereof | |
MX2014002484A (en) | Compounds and compositions as c-kit kinase inhibitors. | |
CA2731432A1 (en) | Tri-cyclic pyrazolopyridine kinase inhibitors | |
AU2017372377B2 (en) | Imidazo [1,5-a] pyrazine derivatives as PI3Kdelta inhibitors | |
TW202116735A (en) | 2h-indazole derivatives and their use in the treatment of disease | |
WO2021219070A1 (en) | Degradation of bruton's tyrosine kinase (btk) by conjugation of btk inhibitors with e3 ligase ligand and methods of use | |
TW202115075A (en) | IMIDAZO[1,2-a]PYRIDINYL DERIVATIVES AND THEIR USE IN THE TREATMENT OF DISEASE | |
EP3980425A1 (en) | Heterocyclic compounds as kinase inhibitors, compositions comprising the heterocyclic compound, and methods of use thereof | |
WO2021180103A1 (en) | Degradation of bruton's tyrosine kinase (btk) by conjugation of btk inhibitors with e3 ligase ligand and methods of use | |
WO2021170046A1 (en) | Tyk-2 inhibitor | |
JP6816287B2 (en) | Pyridine and 5-membered aromatic ring compounds, their production methods and uses | |
WO2023011456A1 (en) | Pyrazolopyridinone compounds | |
US20240025906A1 (en) | Kinase modulators and methods of use thereof | |
WO2023185986A1 (en) | Bcl-xl inhibitors | |
WO2023216237A1 (en) | Heterocyclic compounds as kinase inhibitors, compositions, and methods of use thereof | |
EP4222150A1 (en) | 3-[(1h-pyrazol-4-yl)oxy]pyrazin-2-amine compounds as hpk1 inhibitor and use thereof | |
WO2023125908A1 (en) | Degradation of bruton's tyrosine kinase (btk) by conjugation of btk inhibitors with e3 ligase ligand and methods of use | |
WO2024061340A1 (en) | Nampt modulators, preparations, and uses thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 21829711 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 3183368 Country of ref document: CA |
|
ENP | Entry into the national phase |
Ref document number: 2022579058 Country of ref document: JP Kind code of ref document: A |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112022025946 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112022025946 Country of ref document: BR Kind code of ref document: A2 Effective date: 20221219 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 2021829711 Country of ref document: EP Effective date: 20230123 |
|
ENP | Entry into the national phase |
Ref document number: 2021294706 Country of ref document: AU Date of ref document: 20210621 Kind code of ref document: A |