CN116589462A - 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 - Google Patents
氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 Download PDFInfo
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- CN116589462A CN116589462A CN202310536658.3A CN202310536658A CN116589462A CN 116589462 A CN116589462 A CN 116589462A CN 202310536658 A CN202310536658 A CN 202310536658A CN 116589462 A CN116589462 A CN 116589462A
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- Prior art keywords
- pyridin
- alkyl
- trifluoromethyl
- pyrrolo
- phenyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 178
- 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 description 4
- 150000003839 salts Chemical class 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- -1 cyano, Phenyl Chemical group 0.000 claims description 36
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical group 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 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 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 abstract description 45
- 238000000034 method Methods 0.000 abstract description 29
- 201000011510 cancer Diseases 0.000 abstract description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 17
- 201000010099 disease Diseases 0.000 abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 13
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract description 10
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 8
- 208000036142 Viral infection Diseases 0.000 abstract description 8
- 208000027866 inflammatory disease Diseases 0.000 abstract description 8
- 208000015122 neurodegenerative disease Diseases 0.000 abstract description 8
- 230000009385 viral infection Effects 0.000 abstract description 8
- 208000024172 Cardiovascular disease Diseases 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 description 111
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 109
- 239000000543 intermediate Substances 0.000 description 93
- 239000000047 product Substances 0.000 description 89
- 238000004949 mass spectrometry Methods 0.000 description 79
- 235000002639 sodium chloride Nutrition 0.000 description 65
- 235000019439 ethyl acetate Nutrition 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 238000005481 NMR spectroscopy Methods 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
- 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- 239000012267 brine Substances 0.000 description 20
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 239000003814 drug Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 206010021143 Hypoxia Diseases 0.000 description 15
- 125000005843 halogen group Chemical group 0.000 description 15
- 101000605630 Homo sapiens Phosphatidylinositol 3-kinase catalytic subunit type 3 Proteins 0.000 description 14
- 102100038329 Phosphatidylinositol 3-kinase catalytic subunit type 3 Human genes 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 14
- 230000001146 hypoxic effect Effects 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- 229930195734 saturated hydrocarbon Natural products 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 238000003556 assay Methods 0.000 description 10
- 230000004900 autophagic degradation Effects 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 101150003085 Pdcl gene Proteins 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 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
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
- 206010005003 Bladder cancer Diseases 0.000 description 7
- 206010006187 Breast cancer Diseases 0.000 description 7
- 208000026310 Breast neoplasm Diseases 0.000 description 7
- 206010008342 Cervix carcinoma Diseases 0.000 description 7
- 206010009944 Colon cancer Diseases 0.000 description 7
- 208000032612 Glial tumor Diseases 0.000 description 7
- 206010018338 Glioma Diseases 0.000 description 7
- 208000008839 Kidney Neoplasms Diseases 0.000 description 7
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 7
- 206010025323 Lymphomas Diseases 0.000 description 7
- 206010033128 Ovarian cancer Diseases 0.000 description 7
- 206010061535 Ovarian neoplasm Diseases 0.000 description 7
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 7
- 206010060862 Prostate cancer Diseases 0.000 description 7
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 7
- 206010038389 Renal cancer Diseases 0.000 description 7
- 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 description 7
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 7
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 7
- 201000010881 cervical cancer Diseases 0.000 description 7
- 208000029742 colonic neoplasm Diseases 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 201000010982 kidney cancer Diseases 0.000 description 7
- 208000032839 leukemia Diseases 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 201000007270 liver cancer Diseases 0.000 description 7
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- 201000005202 lung cancer Diseases 0.000 description 7
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- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 7
- 201000003733 ovarian melanoma Diseases 0.000 description 7
- 201000002528 pancreatic cancer Diseases 0.000 description 7
- 208000008443 pancreatic carcinoma Diseases 0.000 description 7
- 208000022679 triple-negative breast carcinoma Diseases 0.000 description 7
- 201000005112 urinary bladder cancer Diseases 0.000 description 7
- 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
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002246 antineoplastic agent Substances 0.000 description 6
- 239000003795 chemical substances by application 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 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
- 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 5
- 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 5
- 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 5
- 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 5
- CXYDPZLJNIQRAZ-UHFFFAOYSA-N 4-(2-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-6-[4-ethylsulfonyl-2-(trifluoromethyl)piperazin-1-yl]-1H-pyridin-2-one Chemical compound C1(CC1)C1=CC=2C(=NC=CC=2C2=CC(NC(=C2)N2C(CN(CC2)S(=O)(=O)CC)C(F)(F)F)=O)N1 CXYDPZLJNIQRAZ-UHFFFAOYSA-N 0.000 description 5
- IBNJRAAEJIHRLO-UHFFFAOYSA-N 4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-6-[2-(trifluoromethyl)piperidin-1-yl]-1H-pyridin-2-one Chemical compound CC1=CC=2C(=NC=CC=2C2=CC(NC(=C2)N2C(CCCC2)C(F)(F)F)=O)N1 IBNJRAAEJIHRLO-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 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 5
- 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 5
- WVCHUMKQHSTBKB-UHFFFAOYSA-N 4-ethylsulfonyl-1-[6-[(2-methylpropan-2-yl)oxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]-2-(trifluoromethyl)piperazine Chemical compound C(C)(C)(C)OC1=CC(=CC(=N1)N1C(CN(CC1)S(=O)(=O)CC)C(F)(F)F)B1OC(C(O1)(C)C)(C)C WVCHUMKQHSTBKB-UHFFFAOYSA-N 0.000 description 5
- PUNDGYRIKMMQHI-UHFFFAOYSA-N 6-(2-chlorophenyl)-4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyridin-2-one Chemical compound ClC1=C(C=CC=C1)C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC(=C2)C PUNDGYRIKMMQHI-UHFFFAOYSA-N 0.000 description 5
- KUHXRVPOFWEIIL-UHFFFAOYSA-N 6-(2-chlorophenyl)-4-(2-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyridin-2-one Chemical compound ClC1=C(C=CC=C1)C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC(=C2)C=1C=NC=CC=1 KUHXRVPOFWEIIL-UHFFFAOYSA-N 0.000 description 5
- IBWQEYYDUJEVFR-UHFFFAOYSA-N 6-(2-chlorophenyl)-4-[2-(1,3-oxazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyridin-2-one Chemical compound ClC1=C(C=CC=C1)C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC(=C2)C1=CN=CO1 IBWQEYYDUJEVFR-UHFFFAOYSA-N 0.000 description 5
- WWHGOOFSNVJOAU-UHFFFAOYSA-N 6-(2-phenylpyrrolidin-1-yl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyridin-2-one Chemical compound C1(=CC=CC=C1)C1N(CCC1)C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC=C2 WWHGOOFSNVJOAU-UHFFFAOYSA-N 0.000 description 5
- FPZSPEGMNPCQHE-UHFFFAOYSA-N 6-(3-methylpyridin-4-yl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyridin-2-one Chemical compound CC=1C=NC=CC=1C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC=C2 FPZSPEGMNPCQHE-UHFFFAOYSA-N 0.000 description 5
- HUCPWIDCPVSLDW-UHFFFAOYSA-N 6-[2-(trifluoromethyl)piperidin-1-yl]-4-[2-[2-(trifluoromethyl)pyrimidin-5-yl]-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyridin-2-one Chemical compound FC(C1N(CCCC1)C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC(=C2)C=1C=NC(=NC=1)C(F)(F)F)(F)F HUCPWIDCPVSLDW-UHFFFAOYSA-N 0.000 description 5
- LRTZISIKPSKAIP-UHFFFAOYSA-N 6-[2-(trifluoromethyl)piperidin-1-yl]-4-[2-[5-(trifluoromethyl)pyridin-3-yl]-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyridin-2-one Chemical compound FC(C1N(CCCC1)C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC(=C2)C=1C=NC=C(C=1)C(F)(F)F)(F)F LRTZISIKPSKAIP-UHFFFAOYSA-N 0.000 description 5
- SCKYJZZLWPCYAC-UHFFFAOYSA-N 6-[2-(trifluoromethyl)piperidin-1-yl]-4-[2-[6-(trifluoromethyl)pyridin-3-yl]-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyridin-2-one Chemical compound FC(C1N(CCCC1)C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC(=C2)C=1C=NC(=CC=1)C(F)(F)F)(F)F SCKYJZZLWPCYAC-UHFFFAOYSA-N 0.000 description 5
- LDLMFSXKVWKENB-UHFFFAOYSA-N 6-[3-(trifluoromethyl)morpholin-4-yl]-4-[2-[3-(trifluoromethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyridin-2-one Chemical compound FC(C1N(CCOC1)C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC(=C2)C1=CC(=CC=C1)C(F)(F)F)(F)F LDLMFSXKVWKENB-UHFFFAOYSA-N 0.000 description 5
- DNRNHHBDLRQHAU-UHFFFAOYSA-N 6-[4-[(4-fluorophenyl)methylsulfonyl]-2-(trifluoromethyl)piperazin-1-yl]-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyridin-2-one Chemical compound FC1=CC=C(C=C1)CS(=O)(=O)N1CC(N(CC1)C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC=C2)C(F)(F)F DNRNHHBDLRQHAU-UHFFFAOYSA-N 0.000 description 5
- VAWHMYMAEPEZTK-UHFFFAOYSA-N 6-[4-ethylsulfonyl-2-(trifluoromethyl)piperazin-1-yl]-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyridin-2-one Chemical compound C(C)S(=O)(=O)N1CC(N(CC1)C1=CC(=CC(N1)=O)C1=C2C(=NC=C1)NC=C2)C(F)(F)F VAWHMYMAEPEZTK-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000007832 Na2SO4 Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
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- FGEIRKDVPVYBKL-UHFFFAOYSA-N tert-butyl 4-(2,6-dichloropyridin-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate Chemical compound ClC1=NC(=CC(=C1)C1=C2C(=NC=C1)N(C=C2)C(=O)OC(C)(C)C)Cl FGEIRKDVPVYBKL-UHFFFAOYSA-N 0.000 description 1
- GHDNLFGEJLLKEC-UHFFFAOYSA-N tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine-1-carboxylate Chemical compound C1=CN=C2N(C(=O)OC(C)(C)C)C=CC2=C1B1OC(C)(C)C(C)(C)O1 GHDNLFGEJLLKEC-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl 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
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- GOFOMJMAFIFSDO-UHFFFAOYSA-N tributyl-(5-methylthiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(C)S1 GOFOMJMAFIFSDO-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000005751 tumor progression Effects 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 230000028973 vesicle-mediated transport Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/43—Enzymes; Proenzymes; Derivatives thereof
- A61K38/45—Transferases (2)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
- A61N5/00—Radiation therapy
- A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pathology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Radiology & Medical Imaging (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17187519.8 | 2017-08-23 | ||
| EP17187519 | 2017-08-23 | ||
| PCT/EP2018/072785 WO2019038384A1 (en) | 2017-08-23 | 2018-08-23 | AZAINDOLYLPYRIDONE AND DIAZAINDOLYLPYRIDONE COMPOUNDS |
| CN201880054872.2A CN111247144B (zh) | 2017-08-23 | 2018-08-23 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880054872.2A Division CN111247144B (zh) | 2017-08-23 | 2018-08-23 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
Publications (1)
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|---|---|
| CN116589462A true CN116589462A (zh) | 2023-08-15 |
Family
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| CN202310536658.3A Pending CN116589462A (zh) | 2017-08-23 | 2018-08-23 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
| CN201880054872.2A Active CN111247144B (zh) | 2017-08-23 | 2018-08-23 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
| CN202310536605.1A Pending CN116589461A (zh) | 2017-08-23 | 2018-08-23 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201880054872.2A Active CN111247144B (zh) | 2017-08-23 | 2018-08-23 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
| CN202310536605.1A Pending CN116589461A (zh) | 2017-08-23 | 2018-08-23 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
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| Country | Link |
|---|---|
| US (2) | US11498919B2 (enExample) |
| EP (2) | EP4001278A1 (enExample) |
| JP (2) | JP7199738B2 (enExample) |
| KR (1) | KR102731945B1 (enExample) |
| CN (3) | CN116589462A (enExample) |
| AU (1) | AU2018321135B2 (enExample) |
| CA (1) | CA3072861A1 (enExample) |
| CY (1) | CY1124818T1 (enExample) |
| DK (1) | DK3672967T3 (enExample) |
| ES (1) | ES2902346T3 (enExample) |
| HR (1) | HRP20211999T1 (enExample) |
| HU (1) | HUE057818T2 (enExample) |
| IL (3) | IL302355A (enExample) |
| LT (1) | LT3672967T (enExample) |
| PL (1) | PL3672967T3 (enExample) |
| PT (1) | PT3672967T (enExample) |
| RS (1) | RS62785B1 (enExample) |
| SI (1) | SI3672967T1 (enExample) |
| SM (1) | SMT202100718T1 (enExample) |
| TW (2) | TWI785101B (enExample) |
| WO (1) | WO2019038384A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP7199738B2 (ja) * | 2017-08-23 | 2023-01-06 | スプリント バイオサイエンス アクティエボラーグ | アザインドリルピリドンおよびジアザインドリルピリドン化合物 |
| JP2023553807A (ja) | 2020-11-25 | 2023-12-26 | デシフェラ・ファーマシューティカルズ，エルエルシー | 抗ウイルス活性のｖｐｓ３４阻害剤 |
| WO2022115562A1 (en) | 2020-11-25 | 2022-06-02 | Deciphera Pharmaceuticals, Llc | Morpholino derivatives as vsp34 inhibitors for use in the treatment of a viral infection |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010003133A2 (en) * | 2008-07-03 | 2010-01-07 | Exelixis Inc. | Cdk modulators |
| WO2015108881A1 (en) * | 2014-01-14 | 2015-07-23 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| CN111247144A (zh) * | 2017-08-23 | 2020-06-05 | 思普瑞特生物科学公司 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1154024B (it) * | 1982-09-22 | 1987-01-21 | Lepetit Spa | Derivati pridinici e procedimento per la loro produzione |
| RU2435769C2 (ru) | 2005-05-20 | 2011-12-10 | Вертекс Фармасьютикалз Инкорпорейтед | Пирролопиридины, полезные в качестве ингибиторов протеинкиназы |
| JP2013525354A (ja) | 2010-04-19 | 2013-06-20 | アッヴィ・インコーポレイテッド | ピロロピリジン系キナーゼ阻害薬 |
| EA201390917A1 (ru) | 2010-12-21 | 2013-12-30 | Новартис Аг | Дигетероарильные соединения в качестве ингибиторов vps34 |
| HUE024504T2 (en) | 2010-12-23 | 2016-01-28 | Sanofi Sa | Pyrimidine derivatives, a process for their preparation and their use in medicine |
| GB201120317D0 (en) | 2011-11-24 | 2012-01-04 | Queen Mary & Westfield College | Screening method |
| CN103450152B (zh) | 2012-06-04 | 2015-11-18 | 济南海乐医药技术开发有限公司 | 基于吲唑、吲哚或氮杂吲唑、氮杂吲哚的双芳基脲类结构抗肿瘤药物 |
| FR2992314B1 (fr) | 2012-06-22 | 2015-10-16 | Sanofi Sa | Nouveaux derives de 2,3-dihydro-1h-imidazo{1,2-a}pyrimidin-5-one et 1,2,3,4-tetrahydro-pyrimido{1,2-a}pyrimidin-6-one comportant une morpholine substituee, leur preparation et leur utilisation pharmaceutique |
| TN2016000270A1 (en) | 2014-01-14 | 2017-10-06 | Millennium Pharm Inc | Heteroaryls and uses thereof. |
| MA39823A (fr) | 2014-04-03 | 2018-01-09 | Janssen Pharmaceutica Nv | Dérivés de pyridine macrocyclique |
| MA39822A (fr) | 2014-04-03 | 2018-02-06 | Janssen Pharmaceutica Nv | Dérivés de pyrimidine bicycle |
| CA3015045A1 (en) | 2016-02-19 | 2017-08-24 | Sprint Bioscience Ab | 6-aryl-4-morpholin-1-ylpyridone compounds useful for the treatment of cancer and diabetes |
| US11179399B2 (en) | 2016-02-19 | 2021-11-23 | Sprint Bioscience Ab | 6-heterocyclyl-4-morpholin-4-ylpyridine-2-one compounds useful for the treatment of cancer and diabetes |
-
2018
- 2018-08-23 JP JP2020510099A patent/JP7199738B2/ja active Active
- 2018-08-23 DK DK18759307.4T patent/DK3672967T3/da active
- 2018-08-23 IL IL302355A patent/IL302355A/en unknown
- 2018-08-23 CN CN202310536658.3A patent/CN116589462A/zh active Pending
- 2018-08-23 EP EP21196341.8A patent/EP4001278A1/en not_active Withdrawn
- 2018-08-23 RS RS20211605A patent/RS62785B1/sr unknown
- 2018-08-23 TW TW107129491A patent/TWI785101B/zh not_active IP Right Cessation
- 2018-08-23 AU AU2018321135A patent/AU2018321135B2/en active Active
- 2018-08-23 CN CN201880054872.2A patent/CN111247144B/zh active Active
- 2018-08-23 SI SI201830500T patent/SI3672967T1/sl unknown
- 2018-08-23 HR HRP20211999TT patent/HRP20211999T1/hr unknown
- 2018-08-23 US US16/638,727 patent/US11498919B2/en active Active
- 2018-08-23 KR KR1020207006930A patent/KR102731945B1/ko active Active
- 2018-08-23 EP EP18759307.4A patent/EP3672967B1/en active Active
- 2018-08-23 HU HUE18759307A patent/HUE057818T2/hu unknown
- 2018-08-23 SM SM20210718T patent/SMT202100718T1/it unknown
- 2018-08-23 PL PL18759307T patent/PL3672967T3/pl unknown
- 2018-08-23 TW TW111140665A patent/TW202325708A/zh unknown
- 2018-08-23 CN CN202310536605.1A patent/CN116589461A/zh active Pending
- 2018-08-23 LT LTEPPCT/EP2018/072785T patent/LT3672967T/lt unknown
- 2018-08-23 ES ES18759307T patent/ES2902346T3/es active Active
- 2018-08-23 WO PCT/EP2018/072785 patent/WO2019038384A1/en not_active Ceased
- 2018-08-23 CA CA3072861A patent/CA3072861A1/en active Pending
- 2018-08-23 PT PT187593074T patent/PT3672967T/pt unknown
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2020
- 2020-02-20 IL IL272792A patent/IL272792B/en unknown
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2022
- 2022-01-03 CY CY20221100001T patent/CY1124818T1/el unknown
- 2022-04-25 IL IL292482A patent/IL292482B2/en unknown
- 2022-10-11 US US18/045,605 patent/US20230322772A1/en not_active Abandoned
- 2022-12-13 JP JP2022198545A patent/JP2023021277A/ja not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010003133A2 (en) * | 2008-07-03 | 2010-01-07 | Exelixis Inc. | Cdk modulators |
| WO2015108881A1 (en) * | 2014-01-14 | 2015-07-23 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| CN111247144A (zh) * | 2017-08-23 | 2020-06-05 | 思普瑞特生物科学公司 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
| CN116589461A (zh) * | 2017-08-23 | 2023-08-15 | 思普瑞特生物科学公司 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
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