CA2903081A1 - Histone demethylase inhibitors - Google Patents
Histone demethylase inhibitors Download PDFInfo
- Publication number
- CA2903081A1 CA2903081A1 CA2903081A CA2903081A CA2903081A1 CA 2903081 A1 CA2903081 A1 CA 2903081A1 CA 2903081 A CA2903081 A CA 2903081A CA 2903081 A CA2903081 A CA 2903081A CA 2903081 A1 CA2903081 A1 CA 2903081A1
- Authority
- CA
- Canada
- Prior art keywords
- imidazol
- pyridine
- carboxylic acid
- compound
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 108010074870 Histone Demethylases Proteins 0.000 title claims abstract description 19
- 102000008157 Histone Demethylases Human genes 0.000 title claims abstract description 19
- 239000003112 inhibitor Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 459
- 238000000034 method Methods 0.000 claims abstract description 274
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 201000011510 cancer Diseases 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 159
- 125000000217 alkyl group Chemical group 0.000 claims description 145
- 229910052739 hydrogen Inorganic materials 0.000 claims description 140
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 140
- 239000001257 hydrogen Substances 0.000 claims description 139
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
- 125000001072 heteroaryl group Chemical group 0.000 claims description 67
- 125000000623 heterocyclic group Chemical group 0.000 claims description 65
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 58
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 58
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 58
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 54
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical group 0.000 claims description 30
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- -1 imidazole-pyridine derivative compounds Chemical class 0.000 abstract description 177
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
- 238000011282 treatment Methods 0.000 abstract description 13
- 201000010099 disease Diseases 0.000 abstract description 11
- 230000005764 inhibitory process Effects 0.000 abstract description 10
- 206010006187 Breast cancer Diseases 0.000 abstract description 7
- 208000026310 Breast neoplasm Diseases 0.000 abstract description 7
- 206010005003 Bladder cancer Diseases 0.000 abstract description 6
- 206010058467 Lung neoplasm malignant Diseases 0.000 abstract description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 abstract description 5
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 abstract description 5
- 201000005202 lung cancer Diseases 0.000 abstract description 5
- 208000020816 lung neoplasm Diseases 0.000 abstract description 5
- 201000005112 urinary bladder cancer Diseases 0.000 abstract description 5
- 206010060862 Prostate cancer Diseases 0.000 abstract description 4
- 201000001441 melanoma Diseases 0.000 abstract description 4
- 230000001613 neoplastic effect Effects 0.000 abstract description 3
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 483
- 238000002360 preparation method Methods 0.000 description 321
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 171
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 147
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 114
- 238000005160 1H NMR spectroscopy Methods 0.000 description 108
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 58
- 239000000126 substance Substances 0.000 description 58
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 57
- 125000002947 alkylene group Chemical group 0.000 description 56
- REQFDBXEACLQPU-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC(C=2N=CNC=2)=C1 REQFDBXEACLQPU-UHFFFAOYSA-N 0.000 description 53
- 239000000243 solution Substances 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 238000003786 synthesis reaction Methods 0.000 description 45
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- TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 41
- 125000004432 carbon atom Chemical group C* 0.000 description 32
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 31
- 150000003254 radicals Chemical class 0.000 description 29
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 28
- 108010033040 Histones Proteins 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 27
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 23
- 125000001207 fluorophenyl group Chemical group 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 108090000623 proteins and genes Proteins 0.000 description 21
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- 238000003556 assay Methods 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 102100040584 Lysine-specific demethylase 2B Human genes 0.000 description 18
- 230000007062 hydrolysis Effects 0.000 description 18
- 238000006460 hydrolysis reaction Methods 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 101000613625 Homo sapiens Lysine-specific demethylase 4A Proteins 0.000 description 17
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- 210000004027 cell Anatomy 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
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- 101001088893 Homo sapiens Lysine-specific demethylase 4C Proteins 0.000 description 15
- 101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 description 15
- 102100033230 Lysine-specific demethylase 4C Human genes 0.000 description 15
- 102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 description 15
- 238000001514 detection method Methods 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- 235000018102 proteins Nutrition 0.000 description 15
- 102000004169 proteins and genes Human genes 0.000 description 15
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 14
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 14
- 101710105679 Lysine-specific demethylase 2B Proteins 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- UZFKIHMFDWGBKC-UHFFFAOYSA-N pyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=C1.NC(=O)C1=CC=NC=C1 UZFKIHMFDWGBKC-UHFFFAOYSA-N 0.000 description 14
- 102100040598 Lysine-specific demethylase 2A Human genes 0.000 description 13
- 125000003709 fluoroalkyl group Chemical group 0.000 description 13
- 239000000651 prodrug Substances 0.000 description 13
- 229940002612 prodrug Drugs 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 11
- 102000036354 FBXLs Human genes 0.000 description 11
- 108091007025 FBXLs Proteins 0.000 description 11
- 102100033247 Lysine-specific demethylase 5B Human genes 0.000 description 11
- 125000004450 alkenylene group Chemical group 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- 238000007069 methylation reaction Methods 0.000 description 11
- 108090000765 processed proteins & peptides Proteins 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 101001088892 Homo sapiens Lysine-specific demethylase 5A Proteins 0.000 description 10
- 101001088883 Homo sapiens Lysine-specific demethylase 5B Proteins 0.000 description 10
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 10
- 101710105678 Lysine-specific demethylase 2A Proteins 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- HWXBTNAVRSUOJR-UHFFFAOYSA-N alpha-hydroxyglutaric acid Natural products OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 10
- 229940009533 alpha-ketoglutaric acid Drugs 0.000 description 10
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- 125000004122 cyclic group Chemical group 0.000 description 10
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- 125000005843 halogen group Chemical group 0.000 description 10
- 235000018977 lysine Nutrition 0.000 description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 10
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 10
- 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 10
- NZHDJNMKYDTLEC-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)pyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC(C=2N=CNC=2)=C1 NZHDJNMKYDTLEC-UHFFFAOYSA-N 0.000 description 9
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 9
- 239000004472 Lysine Substances 0.000 description 9
- 102100033246 Lysine-specific demethylase 5A Human genes 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 230000011987 methylation Effects 0.000 description 9
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 8
- 101100477411 Dictyostelium discoideum set1 gene Proteins 0.000 description 8
- 239000007995 HEPES buffer Substances 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
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 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
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- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
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- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A—HUMAN NECESSITIES
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- 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
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
-
- 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
- C07D405/14—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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361783563P | 2013-03-14 | 2013-03-14 | |
| US61/783,563 | 2013-03-14 | ||
| PCT/US2014/026710 WO2014151945A1 (en) | 2013-03-14 | 2014-03-13 | Histone demethylase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2903081A1 true CA2903081A1 (en) | 2014-09-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2903081A Abandoned CA2903081A1 (en) | 2013-03-14 | 2014-03-13 | Histone demethylase inhibitors |
Country Status (7)
| Country | Link |
|---|---|
| US (5) | US9133166B2 (enExample) |
| EP (1) | EP2969007B1 (enExample) |
| JP (1) | JP6276378B2 (enExample) |
| AU (1) | AU2014236711A1 (enExample) |
| CA (1) | CA2903081A1 (enExample) |
| ES (1) | ES2731773T3 (enExample) |
| WO (1) | WO2014151945A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9133166B2 (en) | 2013-03-14 | 2015-09-15 | Quanticel Pharmaceuticals, Inc. | Histone demethylase inhibitors |
| CA2954060A1 (en) | 2014-07-03 | 2016-01-07 | Celgene Quanticel Research, Inc. | Inhibitors of lysine specific demethylase-1 |
| US9896436B2 (en) | 2014-09-16 | 2018-02-20 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| EA201790502A1 (ru) * | 2014-09-16 | 2017-10-31 | Селджен Квонтисел Рисёрч, Инк. | Ингибиторы гистоновых диметилаз |
| JP2016089002A (ja) * | 2014-10-31 | 2016-05-23 | 出光興産株式会社 | ベンゾフラノチオフェン骨格を有するモノマー及びポリマー、及びそのポリマーを用いた有機薄膜太陽電池材料 |
| JP6889661B2 (ja) * | 2015-01-09 | 2021-06-18 | ジェネンテック， インコーポレイテッド | ４，５−ジヒドロイミダゾール誘導体およびヒストンジメチラーゼ（ｋｄｍ２ｂ）インヒビターとしてのその使用 |
| WO2016210292A1 (en) | 2015-06-25 | 2016-12-29 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion, enrichment, and maintenance |
| US20190055212A1 (en) * | 2016-02-16 | 2019-02-21 | Stephen Gwaltney | Histone demethylase inhibitors |
| WO2017161001A1 (en) | 2016-03-15 | 2017-09-21 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion |
| EP3436445B1 (en) * | 2016-03-15 | 2023-09-06 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| US10150754B2 (en) | 2016-04-19 | 2018-12-11 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| EP3246330A1 (en) | 2016-05-18 | 2017-11-22 | Istituto Europeo di Oncologia S.r.l. | Imidazoles as histone demethylase inhibitors |
| ES2969239T3 (es) | 2016-05-27 | 2024-05-17 | Gilead Sciences Inc | Combinación de ledipasvir y sofosbuvir para su uso en el tratamiento de infecciones por el virus de la hepatitis B en humanos |
| BR102017010009A2 (pt) | 2016-05-27 | 2017-12-12 | Gilead Sciences, Inc. | Compounds for the treatment of hepatitis b virus infection |
| JOP20190024A1 (ar) | 2016-08-26 | 2019-02-19 | Gilead Sciences Inc | مركبات بيروليزين بها استبدال واستخداماتها |
| ES2826748T3 (es) | 2016-09-02 | 2021-05-19 | Gilead Sciences Inc | Derivados de 4,6-diamino-pirido[3,2-d]pirimidina como moduladores de receptores de tipo Toll |
| KR102268448B1 (ko) | 2016-09-02 | 2021-06-22 | 길리애드 사이언시즈, 인코포레이티드 | 톨 유사 수용체 조정제 화합물 |
| 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 |
| CN106543092B (zh) * | 2016-10-14 | 2019-05-17 | 华东师范大学 | 1,5-二芳香基-1,2,4-三氮唑类化合物及其制药用途 |
| TWI868958B (zh) | 2017-01-31 | 2025-01-01 | 美商基利科學股份有限公司 | 替諾福韋埃拉酚胺(tenofovir alafenamide)之晶型 |
| JOP20180008A1 (ar) | 2017-02-02 | 2019-01-30 | Gilead Sciences Inc | مركبات لعلاج إصابة بعدوى فيروس الالتهاب الكبدي b |
| JOP20180040A1 (ar) | 2017-04-20 | 2019-01-30 | Gilead Sciences Inc | مثبطات pd-1/pd-l1 |
| EP3728283B1 (en) | 2017-12-20 | 2023-11-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 3'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| CN111511754B (zh) | 2017-12-20 | 2023-09-12 | 捷克共和国有机化学与生物化学研究所 | 活化sting转接蛋白的具有膦酸酯键的2’3’环状二核苷酸 |
| WO2019160882A1 (en) | 2018-02-13 | 2019-08-22 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| KR102526964B1 (ko) | 2018-02-26 | 2023-04-28 | 길리애드 사이언시즈, 인코포레이티드 | Hbv 복제 억제제로서의 치환된 피롤리진 화합물 |
| WO2019195181A1 (en) | 2018-04-05 | 2019-10-10 | Gilead Sciences, Inc. | Antibodies and fragments thereof that bind hepatitis b virus protein x |
| 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 |
| 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 |
| TW201945388A (zh) | 2018-04-12 | 2019-12-01 | 美商精密生物科學公司 | 對b型肝炎病毒基因體中之識別序列具有特異性之最佳化之經工程化巨核酸酶 |
| WO2019204609A1 (en) | 2018-04-19 | 2019-10-24 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| US20190359645A1 (en) | 2018-05-03 | 2019-11-28 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2'3'-cyclic dinucleotides comprising carbocyclic nucleotide |
| WO2019236766A1 (en) | 2018-06-06 | 2019-12-12 | Ideaya Biosciences, Inc. | Methods of culturing and/or expanding stem cells and/or lineage committed progenitor cells using lactam compounds |
| BR112020026746A2 (pt) | 2018-07-13 | 2021-03-30 | Gilead Sciences, Inc. | Composto, composição farmacêutica, métodos para inibir pd-1, pd-l1 e/ou a interação de pd-1/pd-l1 e para tratar câncer, e, kit para tratar ou prevenir câncer ou uma doença ou condição. |
| WO2020028097A1 (en) | 2018-08-01 | 2020-02-06 | Gilead Sciences, Inc. | Solid forms of (r)-11-(methoxymethyl)-12-(3-methoxypropoxy)-3,3-dimethyl-8-0x0-2,3,8,13b-tetrahydro-1h-pyrido[2,1-a]pyrrolo[1,2-c] phthalazine-7-c arboxylic acid |
| CN112955435B (zh) | 2018-10-24 | 2024-09-06 | 吉利德科学公司 | Pd-1/pd-l1抑制剂 |
| KR102658602B1 (ko) | 2018-10-31 | 2024-04-19 | 길리애드 사이언시즈, 인코포레이티드 | Hpk1 억제 활성을 갖는 치환된 6-아자벤즈이미다졸 화합물 |
| FI3873903T3 (fi) | 2018-10-31 | 2024-03-26 | Gilead Sciences Inc | Substituoituja 6-azabentsiimidatsoliyhdisteitä HPK1-inhibiittoreina |
| EP3934757B1 (en) | 2019-03-07 | 2023-02-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 2'3'-cyclic dinucleotides and prodrugs thereof |
| EP3935065A1 (en) | 2019-03-07 | 2022-01-12 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 3'3'-cyclic dinucleotide analogue comprising a cyclopentanyl modified nucleotide as sting modulator |
| CA3129011C (en) | 2019-03-07 | 2023-12-19 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3'-cyclic dinucleotides and prodrugs thereof |
| TWI751517B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| 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 |
| TWI826690B (zh) | 2019-05-23 | 2023-12-21 | 美商基利科學股份有限公司 | 經取代之烯吲哚酮化物及其用途 |
| JP7237311B2 (ja) * | 2019-06-06 | 2023-03-13 | 京都府公立大学法人 | 化合物、医薬組成物、ｋｄｍ５ｃ阻害剤及び抗うつ剤 |
| MX2021015452A (es) | 2019-06-25 | 2022-02-11 | Gilead Sciences Inc | Proteinas de fusion flt3l-fc y metodos de uso. |
| WO2021011891A1 (en) | 2019-07-18 | 2021-01-21 | Gilead Sciences, Inc. | Long-acting formulations of tenofovir alafenamide |
| WO2021034804A1 (en) | 2019-08-19 | 2021-02-25 | Gilead Sciences, Inc. | Pharmaceutical formulations of tenofovir alafenamide |
| KR20220074917A (ko) | 2019-09-30 | 2022-06-03 | 길리애드 사이언시즈, 인코포레이티드 | Hbv 백신 및 hbv를 치료하는 방법 |
| DK4069729T3 (da) | 2019-12-06 | 2025-04-07 | Prec Biosciences Inc | Optimerede, modificerede meganukleaser med specificitet for en genkendelsessekvens i hepatitis b-virusgenomet |
| AR121620A1 (es) | 2020-03-20 | 2022-06-22 | Gilead Sciences Inc | Profármacos de nucleósidos 4-c-sustituidos-2-halo-2-deoxiadenosina y métodos de preparación y uso de los mismos |
| JP7712352B2 (ja) | 2020-08-07 | 2025-07-23 | ギリアード サイエンシーズ， インコーポレイテッド | ホスホンアミドヌクレオチド類似体のプロドラッグ及びその薬学的使用 |
| TW202406932A (zh) | 2020-10-22 | 2024-02-16 | 美商基利科學股份有限公司 | 介白素2-Fc融合蛋白及使用方法 |
| EP4337223A1 (en) | 2021-05-13 | 2024-03-20 | Gilead Sciences, Inc. | Combination of a tlr8 modulating compound and anti-hbv sirna therapeutics |
| AU2022299051B2 (en) | 2021-06-23 | 2025-03-13 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| KR20240025616A (ko) | 2021-06-23 | 2024-02-27 | 길리애드 사이언시즈, 인코포레이티드 | 다이아실글리세롤 키나제 조절 화합물 |
| KR20240005901A (ko) | 2021-06-23 | 2024-01-12 | 길리애드 사이언시즈, 인코포레이티드 | 디아실글리세롤 키나제 조절 화합물 |
| AU2022298639C1 (en) | 2021-06-23 | 2025-07-17 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| KR20250099113A (ko) | 2022-09-09 | 2025-07-01 | 이노보 테라퓨틱스 인코포레이티드 | CK1α 및 DUAL CK1α/GSPT1 분해 화합물 |
| 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 |
| WO2025240246A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| WO2025240242A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| US20250345389A1 (en) | 2024-05-13 | 2025-11-13 | Gilead Sciences, Inc. | Combination therapies |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU3127900A (en) | 1998-12-23 | 2000-07-31 | Du Pont Pharmaceuticals Company | Thrombin or factor xa inhibitors |
| AU3980602A (en) | 2000-10-26 | 2002-06-03 | Tularik Inc | Antiinflammation agents |
| US20040127733A1 (en) | 2002-10-31 | 2004-07-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New beta-agonists, processes for preparing them and their use as pharmaceutical compositions |
| DE102004021779A1 (de) | 2004-04-30 | 2005-11-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| JP2009519998A (ja) | 2005-12-19 | 2009-05-21 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | アミノアルコール誘導体の過活動膀胱の治療の為の使用 |
| JP4388997B2 (ja) * | 2006-09-05 | 2009-12-24 | 協和発酵キリン株式会社 | イミダゾール誘導体 |
| AU2008242720A1 (en) * | 2007-04-20 | 2008-10-30 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| GB0818907D0 (en) * | 2008-10-15 | 2008-11-19 | Isis Innovation | Histone lysine demethylase inhibitors |
| US20120101099A1 (en) * | 2009-07-07 | 2012-04-26 | Anthem Biosciences Private Limited | Histone deacetylase inhibitors |
| CN102695708B (zh) | 2009-11-10 | 2014-10-15 | 辉瑞大药厂 | N1-吡唑并螺酮乙酰辅酶a羧化酶抑制剂 |
| WO2011089995A1 (ja) * | 2010-01-21 | 2011-07-28 | 公立大学法人名古屋市立大学 | ヒドロキサム酸誘導体及びそれを用いたｈｄａｃ８阻害剤 |
| GB201112607D0 (en) * | 2011-07-22 | 2011-09-07 | Glaxo Group Ltd | Novel compounds |
| CN102775368B (zh) * | 2011-05-10 | 2016-08-17 | 上海驺虞医药科技有限公司 | 一类噻唑类化合物及其制备方法和用途 |
| US9133166B2 (en) * | 2013-03-14 | 2015-09-15 | Quanticel Pharmaceuticals, Inc. | Histone demethylase inhibitors |
| EA201790502A1 (ru) | 2014-09-16 | 2017-10-31 | Селджен Квонтисел Рисёрч, Инк. | Ингибиторы гистоновых диметилаз |
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