ES2997267T3 - Azole-fused pyridazin-3(2h)-one derivatives - Google Patents
Azole-fused pyridazin-3(2h)-one derivatives Download PDFInfo
- Publication number
- ES2997267T3 ES2997267T3 ES20781670T ES20781670T ES2997267T3 ES 2997267 T3 ES2997267 T3 ES 2997267T3 ES 20781670 T ES20781670 T ES 20781670T ES 20781670 T ES20781670 T ES 20781670T ES 2997267 T3 ES2997267 T3 ES 2997267T3
- Authority
- ES
- Spain
- Prior art keywords
- oxo
- hydro
- acetam
- met
- ethyl
- 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.)
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- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 509
- 150000003839 salts Chemical class 0.000 claims abstract description 79
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 40
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 208000035475 disorder Diseases 0.000 claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 308
- -1 cyano, hydroxy Chemical group 0.000 claims description 197
- 125000005843 halogen group Chemical group 0.000 claims description 133
- 125000001424 substituent group Chemical group 0.000 claims description 116
- 229910052739 hydrogen Inorganic materials 0.000 claims description 107
- 239000001257 hydrogen Substances 0.000 claims description 107
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 61
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 31
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 30
- YNTJKQDWYXUTLZ-UHFFFAOYSA-N 2-(3-chlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC(Cl)=C1 YNTJKQDWYXUTLZ-UHFFFAOYSA-N 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 24
- 125000006413 ring segment Chemical group 0.000 claims description 24
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 23
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 17
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 208000011117 substance-related disease Diseases 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 201000000980 schizophrenia Diseases 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims description 7
- 208000010877 cognitive disease Diseases 0.000 claims description 6
- 208000020925 Bipolar disease Diseases 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 201000009032 substance abuse Diseases 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 208000028698 Cognitive impairment Diseases 0.000 claims description 4
- 208000030814 Eating disease Diseases 0.000 claims description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
- 208000001640 Fibromyalgia Diseases 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 208000029560 autism spectrum disease Diseases 0.000 claims description 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- 206010013663 drug dependence Diseases 0.000 claims description 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- 231100000736 substance abuse Toxicity 0.000 claims description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- LMMZNDAFKZTCFU-ZDUSSCGKSA-N C(C)(C)N1N=C(C2=C1C=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC)C Chemical compound C(C)(C)N1N=C(C2=C1C=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC)C LMMZNDAFKZTCFU-ZDUSSCGKSA-N 0.000 claims 1
- LTKRJEYSSHZTTH-AWEZNQCLSA-N C1(CC1)C1=NN(C=2C=NN(C(C=21)=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC)C(C)C Chemical compound C1(CC1)C1=NN(C=2C=NN(C(C=21)=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC)C(C)C LTKRJEYSSHZTTH-AWEZNQCLSA-N 0.000 claims 1
- LISAPNDPWWHHBH-LBPRGKRZSA-N FC=1C=C(C=CC=1OC)[C@H](C)NC(CN1N=C(C2=C(C1=O)C(=NN2C)C(C)C)C)=O Chemical compound FC=1C=C(C=CC=1OC)[C@H](C)NC(CN1N=C(C2=C(C1=O)C(=NN2C)C(C)C)C)=O LISAPNDPWWHHBH-LBPRGKRZSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 50
- 101000996780 Homo sapiens Probable G-protein coupled receptor 139 Proteins 0.000 abstract description 33
- 102100033836 Probable G-protein coupled receptor 139 Human genes 0.000 abstract description 30
- 239000000463 material Substances 0.000 abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 283
- 239000007787 solid Substances 0.000 description 224
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 210
- 239000000243 solution Substances 0.000 description 166
- 239000000203 mixture Substances 0.000 description 160
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 145
- 235000019439 ethyl acetate Nutrition 0.000 description 140
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 136
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 108
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 100
- 238000002360 preparation method Methods 0.000 description 97
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 88
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
- 239000011541 reaction mixture Substances 0.000 description 82
- 239000003208 petroleum Substances 0.000 description 66
- 238000005160 1H NMR spectroscopy Methods 0.000 description 65
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
- 239000012044 organic layer Substances 0.000 description 58
- 239000007832 Na2SO4 Substances 0.000 description 56
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 56
- 229910052938 sodium sulfate Inorganic materials 0.000 description 56
- 235000011152 sodium sulphate Nutrition 0.000 description 56
- 230000002829 reductive effect Effects 0.000 description 55
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 50
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 48
- 239000012267 brine Substances 0.000 description 48
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 48
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 45
- 238000004440 column chromatography Methods 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 30
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
- 239000002904 solvent Substances 0.000 description 29
- 238000009472 formulation Methods 0.000 description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 26
- 239000012065 filter cake Substances 0.000 description 26
- 229910000027 potassium carbonate Inorganic materials 0.000 description 25
- 229920006395 saturated elastomer Polymers 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 21
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- 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 18
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- ZSYGWJREJLLXFB-ZETCQYMHSA-N (1s)-1-(2-fluoro-4-methylphenyl)ethanamine Chemical compound C[C@H](N)C1=CC=C(C)C=C1F ZSYGWJREJLLXFB-ZETCQYMHSA-N 0.000 description 15
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- 125000006239 protecting group Chemical group 0.000 description 11
- UZDDXUMOXKDXNE-QMMMGPOBSA-N (1s)-1-(4-methylphenyl)ethanamine Chemical compound C[C@H](N)C1=CC=C(C)C=C1 UZDDXUMOXKDXNE-QMMMGPOBSA-N 0.000 description 10
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- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 150000004677 hydrates Chemical class 0.000 description 9
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 9
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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 8
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 8
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- 238000012746 preparative thin layer chromatography Methods 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 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 7
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 6
- HGXJOXHYPGNVNK-UHFFFAOYSA-N butane;ethenoxyethane;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C)OCC HGXJOXHYPGNVNK-UHFFFAOYSA-N 0.000 description 6
- 235000011089 carbon dioxide Nutrition 0.000 description 6
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- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 6
- 239000013058 crude material Substances 0.000 description 6
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
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- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 229960005318 vigabatrin Drugs 0.000 description 1
- PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 description 1
- 229960003740 vilazodone Drugs 0.000 description 1
- SGEGOXDYSFKCPT-UHFFFAOYSA-N vilazodone Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(OC4=CC=3)C(=O)N)=CNC2=C1 SGEGOXDYSFKCPT-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229960002263 vortioxetine Drugs 0.000 description 1
- YQNWZWMKLDQSAC-UHFFFAOYSA-N vortioxetine Chemical compound CC1=CC(C)=CC=C1SC1=CC=CC=C1N1CCNCC1 YQNWZWMKLDQSAC-UHFFFAOYSA-N 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
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- 239000003871 white petrolatum Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 1
- 229960004010 zaleplon Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US201962901052P | 2019-09-16 | 2019-09-16 | |
| PCT/US2020/050823 WO2021055326A1 (en) | 2019-09-16 | 2020-09-15 | Azole-fused pyridazin-3(2h)-one derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2997267T3 true ES2997267T3 (en) | 2025-02-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ES20781670T Active ES2997267T3 (en) | 2019-09-16 | 2020-09-15 | Azole-fused pyridazin-3(2h)-one derivatives |
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| HR (1) | HRP20250088T1 (enExample) |
| HU (1) | HUE069908T2 (enExample) |
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| MX (1) | MX2022003177A (enExample) |
| PE (1) | PE20221341A1 (enExample) |
| PH (1) | PH12022550597A1 (enExample) |
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| RS (1) | RS66463B1 (enExample) |
| TW (1) | TWI873185B (enExample) |
| WO (1) | WO2021055326A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| PL4031552T3 (pl) | 2019-09-16 | 2025-03-17 | Takeda Pharmaceutical Company Limited | Pochodne azolowo-skondensowanych pirydazyn-3(2h)-onów |
| JP7697974B2 (ja) | 2020-05-08 | 2025-06-24 | 武田薬品工業株式会社 | Ｇｐｒ１３９アゴニストの置換ベンゾトリアジノン代謝物 |
| GB202106872D0 (en) * | 2021-05-13 | 2021-06-30 | Addex Pharmaceuticals Sa | Novel compounds |
| CN114149371B (zh) * | 2021-11-26 | 2023-08-22 | 首都医科大学 | 四取代吡唑类化合物及其应用 |
| WO2023165262A1 (zh) * | 2022-03-01 | 2023-09-07 | 上海科技大学 | 噻吩并含氮杂环类化合物、含其的药物组合物、其制备方法及其应用 |
| US20250163065A1 (en) * | 2022-03-01 | 2025-05-22 | Shanghaitech University | Pyrrolotriazinone compound, pharmaceutical composition comprising same, preparation method therefor, and use thereof |
| IT202200024948A1 (it) * | 2022-12-05 | 2024-06-05 | Angelini Pharma S P A | Composti attivatori dei canali potassio KV7.2/KV7.3 |
| CN116063179A (zh) * | 2023-02-20 | 2023-05-05 | 南京杰运医药科技有限公司 | 一种4-甲氧基乙酰乙酸甲酯的合成方法 |
| WO2025119351A1 (zh) * | 2023-12-08 | 2025-06-12 | 深圳湾实验室 | Gpr139激动剂 |
| WO2025124544A1 (zh) * | 2023-12-14 | 2025-06-19 | 华润医药研究院（深圳）有限公司 | 3,4-二氢-2H-苯并[b][1,4]二氧杂环庚烷类化合物及其制备方法和医药用途 |
| WO2025162441A1 (zh) * | 2024-02-02 | 2025-08-07 | 上海科技大学 | 稠杂环类化合物与其制备方法、药物组合物及应用 |
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2020
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- 2020-09-15 AU AU2020348675A patent/AU2020348675B2/en active Active
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| KR102924294B1 (ko) | 2026-02-09 |
| CR20220160A (es) | 2022-06-16 |
| JOP20220063A1 (ar) | 2023-01-30 |
| JP2022548602A (ja) | 2022-11-21 |
| US12370192B2 (en) | 2025-07-29 |
| EP4031552B1 (en) | 2024-11-06 |
| DOP2022000057A (es) | 2022-06-30 |
| MX2022003177A (es) | 2022-04-06 |
| IL291181B1 (en) | 2025-05-01 |
| EP4031552A1 (en) | 2022-07-27 |
| KR20220063228A (ko) | 2022-05-17 |
| US20230028114A1 (en) | 2023-01-26 |
| BR112022004819A2 (pt) | 2022-06-07 |
| HRP20250088T1 (hr) | 2025-03-28 |
| WO2021055326A1 (en) | 2021-03-25 |
| AU2020348675B2 (en) | 2025-11-20 |
| PL4031552T3 (pl) | 2025-03-17 |
| IL291181B2 (en) | 2025-09-01 |
| TWI873185B (zh) | 2025-02-21 |
| CO2022004684A2 (es) | 2022-07-08 |
| ECSP22020159A (es) | 2022-05-31 |
| JP7566888B2 (ja) | 2024-10-15 |
| HUE069908T2 (hu) | 2025-04-28 |
| RS66463B1 (sr) | 2025-02-28 |
| CA3150508A1 (en) | 2021-03-25 |
| TW202124386A (zh) | 2021-07-01 |
| EP4031552C0 (en) | 2024-11-06 |
| PH12022550597A1 (en) | 2024-03-04 |
| AR119971A1 (es) | 2022-01-26 |
| PE20221341A1 (es) | 2022-09-13 |
| CN114728975A (zh) | 2022-07-08 |
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