AU2022390051A1 - Heterocyclic amides and methods of using the same - Google Patents
Heterocyclic amides and methods of using the same Download PDFInfo
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- AU2022390051A1 AU2022390051A1 AU2022390051A AU2022390051A AU2022390051A1 AU 2022390051 A1 AU2022390051 A1 AU 2022390051A1 AU 2022390051 A AU2022390051 A AU 2022390051A AU 2022390051 A AU2022390051 A AU 2022390051A AU 2022390051 A1 AU2022390051 A1 AU 2022390051A1
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- Prior art keywords
- compound
- alkyl
- mmol
- halogen
- pharmaceutically acceptable
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- 238000000034 method Methods 0.000 title claims abstract description 99
- -1 Heterocyclic amides Chemical class 0.000 title claims description 236
- 150000001875 compounds Chemical class 0.000 claims abstract description 451
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 114
- 150000003839 salts Chemical class 0.000 claims abstract description 114
- 201000010099 disease Diseases 0.000 claims abstract description 78
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 41
- 208000035475 disorder Diseases 0.000 claims abstract description 36
- 150000003384 small molecules Chemical class 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 185
- 229910052736 halogen Inorganic materials 0.000 claims description 132
- 150000002367 halogens Chemical class 0.000 claims description 120
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 74
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 63
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 62
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000000304 alkynyl group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 25
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 24
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims description 24
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 201000003415 fragile X-associated tremor/ataxia syndrome Diseases 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 208000023105 Huntington disease Diseases 0.000 claims description 12
- 239000000651 prodrug Substances 0.000 claims description 12
- 229940002612 prodrug Drugs 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 208000002569 Machado-Joseph Disease Diseases 0.000 claims description 9
- 208000036834 Spinocerebellar ataxia type 3 Diseases 0.000 claims description 9
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 9
- 125000000468 ketone group Chemical group 0.000 claims description 9
- 229930194542 Keto Natural products 0.000 claims description 8
- 201000009340 myotonic dystrophy type 1 Diseases 0.000 claims description 8
- 102100024378 AF4/FMR2 family member 2 Human genes 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 208000001914 Fragile X syndrome Diseases 0.000 claims description 7
- 101000833172 Homo sapiens AF4/FMR2 family member 2 Proteins 0.000 claims description 7
- 101000828537 Homo sapiens Synaptic functional regulator FMR1 Proteins 0.000 claims description 7
- 208000036626 Mental retardation Diseases 0.000 claims description 7
- 208000035955 Proximal myotonic myopathy Diseases 0.000 claims description 7
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- 102100023532 Synaptic functional regulator FMR1 Human genes 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 201000008709 myotonic dystrophy type 2 Diseases 0.000 claims description 7
- 102000007371 Ataxin-3 Human genes 0.000 claims description 6
- 108010032947 Ataxin-3 Proteins 0.000 claims description 6
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- 108010032951 Ataxin2 Proteins 0.000 claims description 6
- 208000024412 Friedreich ataxia Diseases 0.000 claims description 6
- 201000003622 Spinocerebellar ataxia type 2 Diseases 0.000 claims description 6
- 201000003620 Spinocerebellar ataxia type 6 Diseases 0.000 claims description 6
- 201000003629 Spinocerebellar ataxia type 8 Diseases 0.000 claims description 6
- 125000006456 halo alkyl cycloalkyl group Chemical group 0.000 claims description 6
- 239000002773 nucleotide Substances 0.000 claims description 6
- 125000003729 nucleotide group Chemical group 0.000 claims description 6
- 201000003624 spinocerebellar ataxia type 1 Diseases 0.000 claims description 6
- 201000003594 spinocerebellar ataxia type 12 Diseases 0.000 claims description 6
- 201000003570 spinocerebellar ataxia type 17 Diseases 0.000 claims description 6
- 201000003632 spinocerebellar ataxia type 7 Diseases 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 206010068871 Myotonic dystrophy Diseases 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 102100032187 Androgen receptor Human genes 0.000 claims description 3
- 201000004254 Desbuquois dysplasia Diseases 0.000 claims description 3
- 208000025008 Desbuquois dysplasia 2 Diseases 0.000 claims description 3
- 208000000980 Desbuquois syndrome Diseases 0.000 claims description 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 3
- 101000775732 Homo sapiens Androgen receptor Proteins 0.000 claims description 3
- 208000006269 X-Linked Bulbo-Spinal Atrophy Diseases 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims description 3
- 201000008163 Dentatorubral pallidoluysian atrophy Diseases 0.000 claims description 2
- 241000282485 Vulpes vulpes Species 0.000 claims description 2
- 230000003511 endothelial effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 229
- 238000011282 treatment Methods 0.000 abstract description 23
- 241000282414 Homo sapiens Species 0.000 abstract description 17
- 108090000623 proteins and genes Proteins 0.000 abstract description 15
- 230000000694 effects Effects 0.000 abstract description 13
- 241001465754 Metazoa Species 0.000 abstract description 6
- 108020004999 messenger RNA Proteins 0.000 abstract 2
- 230000002068 genetic effect Effects 0.000 abstract 1
- 230000037361 pathway Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 364
- 239000007787 solid Substances 0.000 description 215
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 193
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 174
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 168
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 165
- 229910001868 water Inorganic materials 0.000 description 162
- 239000000047 product Substances 0.000 description 133
- 239000000243 solution Substances 0.000 description 130
- 238000005160 1H NMR spectroscopy Methods 0.000 description 128
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 128
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 112
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 107
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 97
- 235000002639 sodium chloride Nutrition 0.000 description 90
- 239000011541 reaction mixture Substances 0.000 description 84
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 71
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
- 229910052727 yttrium Inorganic materials 0.000 description 58
- 235000019439 ethyl acetate Nutrition 0.000 description 55
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 53
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 48
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 47
- 239000012267 brine Substances 0.000 description 46
- 239000012044 organic layer Substances 0.000 description 44
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 43
- 239000007821 HATU Substances 0.000 description 41
- 239000004698 Polyethylene Substances 0.000 description 41
- 238000003786 synthesis reaction Methods 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 238000000746 purification Methods 0.000 description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 36
- 239000002244 precipitate Substances 0.000 description 33
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000001816 cooling Methods 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000001914 filtration Methods 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- 230000002829 reductive effect Effects 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 125000006239 protecting group Chemical group 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 125000004429 atom Chemical group 0.000 description 20
- 238000004128 high performance liquid chromatography Methods 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- 238000002953 preparative HPLC Methods 0.000 description 20
- 229910052938 sodium sulfate Inorganic materials 0.000 description 20
- 235000011152 sodium sulphate Nutrition 0.000 description 20
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 19
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
- 239000008346 aqueous phase Substances 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 19
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 17
- 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 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
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- 230000008569 process Effects 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 6
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- 229940086542 triethylamine Drugs 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
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- 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
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- 238000013518 transcription Methods 0.000 description 1
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- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000005310 triazolidinyl group Chemical group N1(NNCC1)* 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- DCGLONGLPGISNX-UHFFFAOYSA-N trimethyl(prop-1-ynyl)silane Chemical compound CC#C[Si](C)(C)C DCGLONGLPGISNX-UHFFFAOYSA-N 0.000 description 1
- 229960005066 trisodium edetate Drugs 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 229920001664 tyloxapol Polymers 0.000 description 1
- MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 1
- 229960004224 tyloxapol Drugs 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- 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
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- 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
- C07D487/08—Bridged systems
-
- 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
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202163280939P | 2021-11-18 | 2021-11-18 | |
| US63/280,939 | 2021-11-18 | ||
| PCT/US2022/080182 WO2023092098A1 (en) | 2021-11-18 | 2022-11-18 | Heterocyclic amides and methods of using the same |
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| AU2022390051A1 true AU2022390051A1 (en) | 2024-05-30 |
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| AU2022390051A Pending AU2022390051A1 (en) | 2021-11-18 | 2022-11-18 | Heterocyclic amides and methods of using the same |
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| US (1) | US20250066389A1 (https=) |
| EP (1) | EP4433457A1 (https=) |
| JP (1) | JP2024540532A (https=) |
| KR (1) | KR20240133696A (https=) |
| CN (1) | CN118786117A (https=) |
| AU (1) | AU2022390051A1 (https=) |
| CA (1) | CA3238521A1 (https=) |
| IL (1) | IL312843A (https=) |
| MX (1) | MX2024006065A (https=) |
| TW (1) | TW202334093A (https=) |
| WO (1) | WO2023092098A1 (https=) |
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| WO2025211457A1 (ja) * | 2024-04-05 | 2025-10-09 | 日本新薬株式会社 | Cugリピートrnaとmbnlタンパクとの結合阻害化合物および医薬 |
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| WO2019028440A1 (en) * | 2017-08-04 | 2019-02-07 | Skyhawk Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR MODULATING SPLICING |
| US11129829B2 (en) * | 2019-06-17 | 2021-09-28 | Skyhawk Therapeutics, Inc. | Methods for modulating splicing |
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2022
- 2022-11-18 AU AU2022390051A patent/AU2022390051A1/en active Pending
- 2022-11-18 WO PCT/US2022/080182 patent/WO2023092098A1/en not_active Ceased
- 2022-11-18 EP EP22840846.4A patent/EP4433457A1/en active Pending
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- 2022-11-18 US US18/710,312 patent/US20250066389A1/en active Pending
- 2022-11-18 JP JP2024529550A patent/JP2024540532A/ja active Pending
- 2022-11-18 CN CN202280088076.7A patent/CN118786117A/zh active Pending
Also Published As
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|---|---|
| TW202334093A (zh) | 2023-09-01 |
| WO2023092098A1 (en) | 2023-05-25 |
| KR20240133696A (ko) | 2024-09-04 |
| US20250066389A1 (en) | 2025-02-27 |
| MX2024006065A (es) | 2024-08-14 |
| EP4433457A1 (en) | 2024-09-25 |
| IL312843A (en) | 2024-07-01 |
| CA3238521A1 (en) | 2023-05-25 |
| JP2024540532A (ja) | 2024-10-31 |
| CN118786117A (zh) | 2024-10-15 |
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