HUE034906T2 - Hiszton-demetiláz inhibitorok - Google Patents
Hiszton-demetiláz inhibitorok Download PDFInfo
- Publication number
- HUE034906T2 HUE034906T2 HUE14768099A HUE14768099A HUE034906T2 HU E034906 T2 HUE034906 T2 HU E034906T2 HU E14768099 A HUE14768099 A HU E14768099A HU E14768099 A HUE14768099 A HU E14768099A HU E034906 T2 HUE034906 T2 HU E034906T2
- Authority
- HU
- Hungary
- Prior art keywords
- pyrimidin
- calc
- pyrido
- alkyl
- found
- Prior art date
Links
- 108010074870 Histone Demethylases Proteins 0.000 title description 18
- 102000008157 Histone Demethylases Human genes 0.000 title description 18
- 239000003112 inhibitor Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 372
- -1 carbocyclic aryl radical Chemical class 0.000 claims description 173
- 238000000034 method Methods 0.000 claims description 147
- 125000000217 alkyl group Chemical group 0.000 claims description 123
- 125000000623 heterocyclic group Chemical group 0.000 claims description 95
- 125000001072 heteroaryl group Chemical group 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000002947 alkylene group Chemical group 0.000 claims description 54
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 32
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 28
- 150000003254 radicals Chemical class 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 108010033040 Histones Proteins 0.000 claims description 21
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 201000011510 cancer Diseases 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 102000004190 Enzymes Human genes 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical class OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical group 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 238000009802 hysterectomy Methods 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- ALAGDBVXZZADSN-UHFFFAOYSA-N pentazine Chemical compound C1=NN=NN=N1 ALAGDBVXZZADSN-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 154
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 100
- XIALRQNUNYOSJP-UHFFFAOYSA-N 2-chloro-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1=CC=C2C(O)=NC(Cl)=NC2=C1 XIALRQNUNYOSJP-UHFFFAOYSA-N 0.000 description 92
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 87
- 238000002360 preparation method Methods 0.000 description 80
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- 238000005160 1H NMR spectroscopy Methods 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 62
- 125000004452 carbocyclyl group Chemical group 0.000 description 58
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 39
- 239000007787 solid Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 30
- 150000003839 salts Chemical class 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- PSYHARAGUGWQOG-UHFFFAOYSA-N 2-chloro-8-(1-methylimidazol-4-yl)-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN1C=NC(C=2C3=C(C(N=C(Cl)N3)=O)C=CN=2)=C1 PSYHARAGUGWQOG-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 108090000623 proteins and genes Proteins 0.000 description 15
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 239000000651 prodrug Substances 0.000 description 14
- 229940002612 prodrug Drugs 0.000 description 14
- QXGNHCIXRGPFDC-JTQLQIEISA-N 2-[1-[(3s)-pyrrolidin-3-yl]pyrazol-4-yl]-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1C2=CN=CC=C2C(=O)N=C1C(=C1)C=NN1[C@H]1CCNC1 QXGNHCIXRGPFDC-JTQLQIEISA-N 0.000 description 13
- 101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 description 13
- 102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 description 13
- 125000003709 fluoroalkyl group Chemical group 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- QMOPAFMMLWUTKI-UHFFFAOYSA-N 1h-pyrido[3,4-d]pyrimidin-4-one Chemical class N1=CC=C2C(O)=NC=NC2=C1 QMOPAFMMLWUTKI-UHFFFAOYSA-N 0.000 description 12
- 101001088893 Homo sapiens Lysine-specific demethylase 4C Proteins 0.000 description 12
- 102100033230 Lysine-specific demethylase 4C Human genes 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000001769 aryl amino group Chemical group 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 235000018102 proteins Nutrition 0.000 description 12
- 102000004169 proteins and genes Human genes 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 102000006947 Histones Human genes 0.000 description 10
- 238000003556 assay Methods 0.000 description 10
- GCRITXZUWWISQM-UHFFFAOYSA-N 2-(1-piperidin-4-ylpyrazol-4-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1CCC(CC1)N1N=CC(=C1)OC=1N=C(C2=C(N1)C=NC=C2)O GCRITXZUWWISQM-UHFFFAOYSA-N 0.000 description 9
- YLDNNDOVZCJCTN-NSHDSACASA-N 2-[1-[(3s)-piperidin-3-yl]pyrazol-4-yl]-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1C2=CN=CC=C2C(=O)N=C1C(=C1)C=NN1[C@H]1CCCNC1 YLDNNDOVZCJCTN-NSHDSACASA-N 0.000 description 9
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 description 9
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 9
- 102100033246 Lysine-specific demethylase 5A Human genes 0.000 description 9
- 102100033247 Lysine-specific demethylase 5B Human genes 0.000 description 9
- 235000012054 meals Nutrition 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- QXGNHCIXRGPFDC-SNVBAGLBSA-N 2-[1-[(3r)-pyrrolidin-3-yl]pyrazol-4-yl]-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1C2=CN=CC=C2C(=O)N=C1C(=C1)C=NN1[C@@H]1CCNC1 QXGNHCIXRGPFDC-SNVBAGLBSA-N 0.000 description 8
- 101001088892 Homo sapiens Lysine-specific demethylase 5A Proteins 0.000 description 8
- 101001088883 Homo sapiens Lysine-specific demethylase 5B Proteins 0.000 description 8
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 8
- 239000004472 Lysine Substances 0.000 description 8
- 229910006074 SO2NH2 Inorganic materials 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000004450 alkenylene group Chemical group 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- BELUNASLYMZLPW-UHFFFAOYSA-N 1-benzylpyrazol-4-ol Chemical compound C1=C(O)C=NN1CC1=CC=CC=C1 BELUNASLYMZLPW-UHFFFAOYSA-N 0.000 description 7
- YLDNNDOVZCJCTN-LLVKDONJSA-N 2-[1-[(3r)-piperidin-3-yl]pyrazol-4-yl]-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1C2=CN=CC=C2C(=O)N=C1C(=C1)C=NN1[C@@H]1CCCNC1 YLDNNDOVZCJCTN-LLVKDONJSA-N 0.000 description 7
- 101000613625 Homo sapiens Lysine-specific demethylase 4A Proteins 0.000 description 7
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
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- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 6
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- 101100477411 Dictyostelium discoideum set1 gene Proteins 0.000 description 6
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- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 6
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- 239000008194 pharmaceutical composition Chemical class 0.000 description 6
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- YZRNICKGRPOILY-UHFFFAOYSA-N 1-(1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole Chemical compound C1=C(B2OC(C)(C)C(C)(C)O2)C=NN1C(C)C1=CC=CC=C1 YZRNICKGRPOILY-UHFFFAOYSA-N 0.000 description 5
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- MMQINJPURSSAHV-SNVBAGLBSA-N 2-[1-[(3r)-piperidin-3-yl]pyrazol-4-yl]oxy-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1C2=CN=CC=C2C(=O)N=C1OC(=C1)C=NN1[C@@H]1CCCNC1 MMQINJPURSSAHV-SNVBAGLBSA-N 0.000 description 4
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- IIBSDEGSGLVNOY-UHFFFAOYSA-N (1-ethylpyrazol-4-yl)boronic acid Chemical compound CCN1C=C(B(O)O)C=N1 IIBSDEGSGLVNOY-UHFFFAOYSA-N 0.000 description 3
- MBYQPPXEXWRMQC-UHFFFAOYSA-N (2-chlorophenyl)methanol Chemical compound OCC1=CC=CC=C1Cl MBYQPPXEXWRMQC-UHFFFAOYSA-N 0.000 description 3
- QKJGOHIJTUXQAB-UHFFFAOYSA-N (3-fluoro-5-hydroxyphenyl)-morpholin-4-ylmethanone Chemical compound OC1=CC(F)=CC(C(=O)N2CCOCC2)=C1 QKJGOHIJTUXQAB-UHFFFAOYSA-N 0.000 description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
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- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 239000012453 solvate Substances 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 230000004083 survival effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
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- 150000003892 tartrate salts Chemical class 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- QSQWENQPOSRWLP-UHFFFAOYSA-N tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1N=CC(B2OC(C)(C)C(C)(C)O2)=C1 QSQWENQPOSRWLP-UHFFFAOYSA-N 0.000 description 1
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
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- 125000005985 thienyl[1,3]dithianyl group Chemical group 0.000 description 1
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Classifications
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- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Enzymes And Modification Thereof (AREA)
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| US20150203453A1 (en) | 2012-10-02 | 2015-07-23 | Epitherapeutics Aps | Inhibitors of histone demethylases |
| JP6514117B2 (ja) | 2013-02-27 | 2019-05-15 | エピセラピューティクス アーペーエス | ヒストン脱メチル化酵素の阻害剤 |
| LT2970211T (lt) | 2013-03-15 | 2017-10-25 | Quanticel Pharmaceuticals Inc | Histono demetilazės inhibitoriai |
| CA2957947A1 (en) | 2014-08-27 | 2016-03-03 | Gilead Sciences, Inc. | Compounds and methods for inhibiting histone demethylases |
| US10030017B2 (en) | 2014-09-17 | 2018-07-24 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| AU2015317806A1 (en) | 2014-09-17 | 2017-04-13 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| CN107001358A (zh) | 2014-10-29 | 2017-08-01 | 东亚St株式会社 | 调节组蛋白赖氨酸脱甲基酶(kdm)催化活性的新型吡啶并嘧啶酮化合物 |
| WO2016112251A1 (en) * | 2015-01-09 | 2016-07-14 | Genentech, Inc. | 4,5-dihydroimidazole derivatives and their use as histone demethylase (kdm2b) inhibitors |
| WO2016112284A1 (en) * | 2015-01-09 | 2016-07-14 | Genentech, Inc. | (piperidin-3-yl)(naphthalen-2-yl)methanone derivatives and related compounds as inhibitors of the histone demethylase kdm2b for the treatment of cancer |
| US20170057955A1 (en) * | 2015-08-26 | 2017-03-02 | Dong-A Socio Holdings Co., Ltd. | Pyridopyrimidinone Compounds for Modulating the Catalytic Activity of Histone Lysine Demethylases (KDMs) |
| ES2921009T3 (es) * | 2016-03-15 | 2022-08-16 | Celgene Quanticel Res Inc | Inhibidores de desmetilasas de histonas |
| US10150754B2 (en) | 2016-04-19 | 2018-12-11 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| BR102017010009A2 (pt) | 2016-05-27 | 2017-12-12 | Gilead Sciences, Inc. | Compounds for the treatment of hepatitis b virus infection |
| MX2018014377A (es) | 2016-05-27 | 2019-03-14 | Gilead Sciences Inc | Metodos para tratar infecciones por virus de hepatitis b usando inhibidores de proteina no estructural 5a (ns5a), proteina no estructural 5b (ns5b) o proteina no estructural 3 (ns3). |
| JOP20190024A1 (ar) | 2016-08-26 | 2019-02-19 | Gilead Sciences Inc | مركبات بيروليزين بها استبدال واستخداماتها |
| PT3507276T (pt) | 2016-09-02 | 2022-01-11 | Gilead Sciences Inc | Compostos moduladores do recetor de tipo toll |
| WO2018045150A1 (en) | 2016-09-02 | 2018-03-08 | Gilead Sciences, Inc. | 4,6-diamino-pyrido[3,2-d]pyrimidine derivaties as toll like receptor modulators |
| MA46535A (fr) | 2016-10-14 | 2019-08-21 | Prec Biosciences Inc | Méganucléases modifiées spécifiques de séquences de reconnaissance dans le génome du virus de l'hépatite b |
| TWI714820B (zh) | 2017-01-31 | 2021-01-01 | 美商基利科學股份有限公司 | 替諾福韋艾拉酚胺(tenofovir alafenamide)之晶型 |
| JOP20180008A1 (ar) | 2017-02-02 | 2019-01-30 | Gilead Sciences Inc | مركبات لعلاج إصابة بعدوى فيروس الالتهاب الكبدي b |
| WO2018175670A1 (en) * | 2017-03-22 | 2018-09-27 | The Research Foundation For The State University Of New York | Matrix metalloproteinase-9 hemopexin domain inhibitors and methods of treatment using same |
| JOP20180040A1 (ar) | 2017-04-20 | 2019-01-30 | Gilead Sciences Inc | مثبطات pd-1/pd-l1 |
| WO2019123339A1 (en) | 2017-12-20 | 2019-06-27 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| AU2018392213B2 (en) | 2017-12-20 | 2021-03-04 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3' cyclic dinucleotides with phosphonate bond activating the STING adaptor protein |
| SI3752501T1 (sl) | 2018-02-13 | 2023-08-31 | Gilead Sciences, Inc. | Inhibitorji pd-1/pd-l1 |
| JP7050165B2 (ja) | 2018-02-26 | 2022-04-07 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｂｖ複製阻害剤としての置換ピロリジン化合物 |
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| TWI833744B (zh) | 2018-04-06 | 2024-03-01 | 捷克科學院有機化學與生物化學研究所 | 3'3'-環二核苷酸 |
| TWI818007B (zh) | 2018-04-06 | 2023-10-11 | 捷克科學院有機化學與生物化學研究所 | 2'3'-環二核苷酸 |
| TW202005654A (zh) | 2018-04-06 | 2020-02-01 | 捷克科學院有機化學與生物化學研究所 | ２，２，─環二核苷酸 |
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| JP7158577B2 (ja) | 2018-10-24 | 2022-10-21 | ギリアード サイエンシーズ， インコーポレイテッド | Ｐｄ－１／ｐｄ－ｌ１阻害剤 |
| TWI721624B (zh) | 2018-10-31 | 2021-03-11 | 美商基利科學股份有限公司 | 經取代之6-氮雜苯并咪唑化合物 |
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| TW202210480A (zh) | 2019-04-17 | 2022-03-16 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
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| EP4359389A1 (en) | 2021-06-23 | 2024-05-01 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
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| JP7686091B2 (ja) | 2021-06-23 | 2025-05-30 | ギリアード サイエンシーズ， インコーポレイテッド | ジアシルグリセロールキナーゼ調節化合物 |
| US20250345389A1 (en) | 2024-05-13 | 2025-11-13 | Gilead Sciences, Inc. | Combination therapies |
| WO2025240242A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| WO2025240244A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies comprising bulevirtide and lonafarnib for use in the treatment of hepatitis d virus infection |
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| US5034393A (en) * | 1989-07-27 | 1991-07-23 | Dowelanco | Fungicidal use of pyridopyrimidine, pteridine, pyrimidopyrimidine, pyrimidopyridazine, and pyrimido-1,2,4-triazine derivatives |
| HRP970371A2 (en) * | 1996-07-13 | 1998-08-31 | Kathryn Jane Smith | Heterocyclic compounds |
| ATE468336T1 (de) | 2002-03-15 | 2010-06-15 | Vertex Pharma | Azolylaminoazine als proteinkinasehemmer |
| AR045697A1 (es) * | 2003-07-14 | 2005-11-09 | Arena Pharm Inc | Aril y heteroaril derivados fusionados como moduladores del metabolismo y la prevencion y tratamiento de trastornos relacionados con el mismo |
| US7544677B2 (en) | 2004-08-23 | 2009-06-09 | Merck & Co., Inc. | Inhibitors of Akt activity |
| US20110319409A1 (en) * | 2010-06-23 | 2011-12-29 | Cox Christopher D | 7-aza-quinazoline pde10 inhibitors |
| GB201112607D0 (en) * | 2011-07-22 | 2011-09-07 | Glaxo Group Ltd | Novel compounds |
| LT2970211T (lt) | 2013-03-15 | 2017-10-25 | Quanticel Pharmaceuticals Inc | Histono demetilazės inhibitoriai |
| AU2015317806A1 (en) | 2014-09-17 | 2017-04-13 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
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2014
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| JP2016512834A (ja) | 2016-05-09 |
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| US20160039808A1 (en) | 2016-02-11 |
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| US10526327B2 (en) | 2020-01-07 |
| SMT201700493T1 (it) | 2017-11-15 |
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| EP2970211A1 (en) | 2016-01-20 |
| DK2970211T3 (en) | 2017-10-16 |
| AU2014235280B2 (en) | 2017-08-31 |
| PT2970211T (pt) | 2017-10-31 |
| LT2970211T (lt) | 2017-10-25 |
| EP2970211A4 (en) | 2016-08-03 |
| HRP20171609T1 (hr) | 2017-12-15 |
| ES2644828T3 (es) | 2017-11-30 |
| AU2014235280A1 (en) | 2015-09-17 |
| EP2970211B1 (en) | 2017-07-26 |
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