TW202325708A - 氮雜吲哚基吡啶酮及二氮雜吲哚基吡啶酮化合物 - Google Patents

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Publication number

TW202325708A

TW202325708A TW111140665A TW111140665A TW202325708A TW 202325708 A TW202325708 A TW 202325708A TW 111140665 A TW111140665 A TW 111140665A TW 111140665 A TW111140665 A TW 111140665A TW 202325708 A TW202325708 A TW 202325708A

Authority

TW

Taiwan

Prior art keywords

alkyl

pyridin

phenyl

trifluoromethyl

pyrrolo

Prior art date

2017-08-23

Links

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• SPZROILRMPRYER-UHFFFAOYSA-N 3-(2H-benzotriazol-4-yl)-1H-pyridin-2-one Chemical class N1N=NC2=C(C=CC=C12)C=1C(NC=CC=1)=O SPZROILRMPRYER-UHFFFAOYSA-N 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 130
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
• -1 cyano, phenyl Chemical group 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 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 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims 1
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
• 206010028980 Neoplasm Diseases 0.000 abstract description 32
• 201000011510 cancer Diseases 0.000 abstract description 18
• 238000000034 method Methods 0.000 abstract description 14
• 239000008194 pharmaceutical composition Substances 0.000 abstract description 11
• 238000011282 treatment Methods 0.000 abstract description 10
• 201000010099 disease Diseases 0.000 abstract description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 8
• 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract description 7
• 208000023275 Autoimmune disease Diseases 0.000 abstract description 5
• 208000036142 Viral infection Diseases 0.000 abstract description 5
• 208000027866 inflammatory disease Diseases 0.000 abstract description 5
• 208000015122 neurodegenerative disease Diseases 0.000 abstract description 5
• 230000009385 viral infection Effects 0.000 abstract description 5
• 208000024172 Cardiovascular disease Diseases 0.000 abstract description 4
• 239000000203 mixture Substances 0.000 description 112
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
• 239000000047 product Substances 0.000 description 84
• 235000019439 ethyl acetate Nutrition 0.000 description 55
• 239000000543 intermediate Substances 0.000 description 55
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
• 239000007787 solid Substances 0.000 description 40
• 239000013067 intermediate product Substances 0.000 description 37
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 28
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 239000000741 silica gel Substances 0.000 description 22
• 229910002027 silica gel Inorganic materials 0.000 description 22
• 239000012267 brine Substances 0.000 description 21
• 235000002639 sodium chloride Nutrition 0.000 description 21
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 125000004432 carbon atom Chemical group C* 0.000 description 18
• 239000003814 drug Substances 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• 239000004480 active ingredient Substances 0.000 description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
• 239000007832 Na2SO4 Substances 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
• 238000006243 chemical reaction Methods 0.000 description 15
• 229910052938 sodium sulfate Inorganic materials 0.000 description 15
• 235000011152 sodium sulphate Nutrition 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
• 102100038329 Phosphatidylinositol 3-kinase catalytic subunit type 3 Human genes 0.000 description 14
• 101000605630 Homo sapiens Phosphatidylinositol 3-kinase catalytic subunit type 3 Proteins 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 12
• 239000010410 layer Substances 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
• 238000003556 assay Methods 0.000 description 11
• 239000002585 base Substances 0.000 description 11
• 239000002244 precipitate Substances 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• 101150003085 Pdcl gene Proteins 0.000 description 10
• 230000004900 autophagic degradation Effects 0.000 description 10
• 125000001153 fluoro group Chemical group F* 0.000 description 10
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 9
• 206010021143 Hypoxia Diseases 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• 239000000725 suspension Substances 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
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 230000001146 hypoxic effect Effects 0.000 description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
• 239000003826 tablet Substances 0.000 description 8
• 238000001816 cooling Methods 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 150000002430 hydrocarbons Chemical group 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 239000012071 phase Substances 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 229930195734 saturated hydrocarbon Natural products 0.000 description 7
• MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 6
• JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• 239000003085 diluting agent Substances 0.000 description 6
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• 239000002953 phosphate buffered saline Substances 0.000 description 6
• 238000002953 preparative HPLC Methods 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• 239000012265 solid product Substances 0.000 description 6
• 229940124597 therapeutic agent Drugs 0.000 description 6
• 102000004190 Enzymes Human genes 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 238000005516 engineering process Methods 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
• 239000000546 pharmaceutical excipient Substances 0.000 description 5
• 229920001223 polyethylene glycol Polymers 0.000 description 5
• YEKZXKVUBUHSTI-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-[2-(trifluoromethyl)phenyl]pyridine Chemical compound C(C)(C)(C)OC1=NC(=CC(=C1)B1OC(C(O1)(C)C)(C)C)C1=C(C=CC=C1)C(F)(F)F YEKZXKVUBUHSTI-UHFFFAOYSA-N 0.000 description 4
• ZTLRFJODULZNEQ-UHFFFAOYSA-N 2-chloro-6-[(2-methylpropan-2-yl)oxy]-4-phenylmethoxypyridine Chemical compound C(C1=CC=CC=C1)OC1=CC(=NC(=C1)Cl)OC(C)(C)C ZTLRFJODULZNEQ-UHFFFAOYSA-N 0.000 description 4
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
• DWOZNANUEDYIOF-UHFFFAOYSA-L 4-ditert-butylphosphanyl-n,n-dimethylaniline;dichloropalladium Chemical compound Cl[Pd]Cl.CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1.CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1 DWOZNANUEDYIOF-UHFFFAOYSA-L 0.000 description 4
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
• 206010005003 Bladder cancer Diseases 0.000 description 4
• 206010006187 Breast cancer Diseases 0.000 description 4
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• 206010008342 Cervix carcinoma Diseases 0.000 description 4
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• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• 208000032612 Glial tumor Diseases 0.000 description 4
• 206010018338 Glioma Diseases 0.000 description 4
• 208000008839 Kidney Neoplasms Diseases 0.000 description 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 4
• 206010025323 Lymphomas Diseases 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• 206010033128 Ovarian cancer Diseases 0.000 description 4
• 206010061535 Ovarian neoplasm Diseases 0.000 description 4
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 4
• 239000002202 Polyethylene glycol Substances 0.000 description 4
• 206010060862 Prostate cancer Diseases 0.000 description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• 206010038389 Renal cancer Diseases 0.000 description 4
• 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 description 4
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 4
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 4
• 235000011054 acetic acid Nutrition 0.000 description 4
• 125000003118 aryl group Chemical group 0.000 description 4
• 201000010881 cervical cancer Diseases 0.000 description 4
• 235000019253 formic acid Nutrition 0.000 description 4
• 239000003112 inhibitor Substances 0.000 description 4
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• 201000005202 lung cancer Diseases 0.000 description 4
• 208000020816 lung neoplasm Diseases 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
• 235000019341 magnesium sulphate Nutrition 0.000 description 4
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 4
• 201000001441 melanoma Diseases 0.000 description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
• 201000002528 pancreatic cancer Diseases 0.000 description 4
• 208000008443 pancreatic carcinoma Diseases 0.000 description 4
• 150000003905 phosphatidylinositols Chemical class 0.000 description 4
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 208000022679 triple-negative breast carcinoma Diseases 0.000 description 4
• 201000005112 urinary bladder cancer Diseases 0.000 description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
• QPWQKQNKRKXWCK-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-[2-(trifluoromethyl)piperidin-1-yl]pyridine Chemical compound C(C)(C)(C)OC1=NC(=CC(=C1)B1OC(C(O1)(C)C)(C)C)N1C(CCCC1)C(F)(F)F QPWQKQNKRKXWCK-UHFFFAOYSA-N 0.000 description 3
• QVXZGMUKOWYSOX-UHFFFAOYSA-N 4-(1H-pyrazolo[3,4-b]pyridin-4-yl)-6-[2-(trifluoromethyl)piperidin-1-yl]-1H-pyridin-2-one Chemical compound N1N=CC=2C1=NC=CC=2C1=CC(NC(=C1)N1C(CCCC1)C(F)(F)F)=O QVXZGMUKOWYSOX-UHFFFAOYSA-N 0.000 description 3
• CSXOYNVGINDZNB-UHFFFAOYSA-N 4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-6-[2-(trifluoromethyl)phenyl]-1H-pyridin-2-one Chemical compound N1C=CC=2C1=NC=CC=2C1=CC(NC(=C1)C1=C(C=CC=C1)C(F)(F)F)=O CSXOYNVGINDZNB-UHFFFAOYSA-N 0.000 description 3
• DOJFVPVHXQICAN-UHFFFAOYSA-N 4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-6-[2-(trifluoromethyl)piperidin-1-yl]-1H-pyridin-2-one Chemical compound N1C=CC=2C1=NC=CC=2C1=CC(NC(=C1)N1C(CCCC1)C(F)(F)F)=O DOJFVPVHXQICAN-UHFFFAOYSA-N 0.000 description 3
• JDKCFBIRILXMFJ-UHFFFAOYSA-N 4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-6-[3-(trifluoromethyl)morpholin-4-yl]-1H-pyridin-2-one Chemical compound N1C=CC=2C1=NC=CC=2C1=CC(NC(=C1)N1C(COCC1)C(F)(F)F)=O JDKCFBIRILXMFJ-UHFFFAOYSA-N 0.000 description 3
• SDFBGSCILLFDMY-UHFFFAOYSA-N 4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-6-morpholin-4-yl-1H-pyridin-2-one Chemical compound CC1=CC=2C(=NC=CC=2C2=CC(NC(=C2)N2CCOCC2)=O)N1 SDFBGSCILLFDMY-UHFFFAOYSA-N 0.000 description 3
• AINQHQYRXCJWMT-UHFFFAOYSA-N 4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-6-pyridin-3-yl-1H-pyridin-2-one Chemical compound CC1=CC=2C(=NC=CC=2C2=CC(NC(=C2)C=2C=NC=CC=2)=O)N1 AINQHQYRXCJWMT-UHFFFAOYSA-N 0.000 description 3
• INUVCRPQYQBTTA-UHFFFAOYSA-N 4-[2-(5-methylthiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-6-[3-(trifluoromethyl)morpholin-4-yl]-1H-pyridin-2-one Chemical compound CC1=CC=C(S1)C1=CC=2C(=NC=CC=2C2=CC(NC(=C2)N2C(COCC2)C(F)(F)F)=O)N1 INUVCRPQYQBTTA-UHFFFAOYSA-N 0.000 description 3
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