TW202345836A - 可用作ＮＬＲＰ３衍生物之吡啶并－〔３，４－ｄ〕噠嗪胺衍生物 - Google Patents

Info

Publication number

TW202345836A

TW202345836A TW112111280A TW112111280A TW202345836A TW 202345836 A TW202345836 A TW 202345836A TW 112111280 A TW112111280 A TW 112111280A TW 112111280 A TW112111280 A TW 112111280A TW 202345836 A TW202345836 A TW 202345836A

Authority

TW

Taiwan

Prior art keywords

compound

pyrido

amino

pyridazin

phenol

Prior art date

2022-03-25

Links

• Espacenet
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• IHYJXEQIZYROGA-UHFFFAOYSA-N pyrido[3,4-d]pyridazine Chemical compound N1=NC=C2C=NC=CC2=C1 IHYJXEQIZYROGA-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 801
• 150000003839 salts Chemical class 0.000 claims abstract description 214
• 239000012453 solvate Substances 0.000 claims abstract description 125
• 239000000651 prodrug Substances 0.000 claims abstract description 116
• 229940002612 prodrug Drugs 0.000 claims abstract description 116
• 238000011282 treatment Methods 0.000 claims abstract description 33
• 125000006413 ring segment Chemical group 0.000 claims abstract description 21
• 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims abstract description 19
• 102000000874 Pyrin Domain-Containing 3 Protein NLR Family Human genes 0.000 claims abstract description 9
• 108010001946 Pyrin Domain-Containing 3 Protein NLR Family Proteins 0.000 claims abstract description 9
• -1 clathrates Chemical class 0.000 claims description 435
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 298
• 229910052736 halogen Inorganic materials 0.000 claims description 186
• 150000002367 halogens Chemical class 0.000 claims description 178
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 168
• 238000000034 method Methods 0.000 claims description 148
• 201000010099 disease Diseases 0.000 claims description 125
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 89
• 239000008194 pharmaceutical composition Substances 0.000 claims description 80
• 150000004677 hydrates Chemical class 0.000 claims description 67
• 208000035475 disorder Diseases 0.000 claims description 43
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 239000003814 drug Substances 0.000 claims description 38
• 239000003937 drug carrier Substances 0.000 claims description 38
• 125000004429 atom Chemical group 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 125000005843 halogen group Chemical group 0.000 claims description 25
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 25
• 208000017169 kidney disease Diseases 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• CNJJEBORDAHQLN-CYBMUJFWSA-N CC(C)(C1)OC[C@@H]1NC1=C(C=NC=C2)C2=C(C(C=CC(C)=C2)=C2O)N=N1 Chemical compound CC(C)(C1)OC[C@@H]1NC1=C(C=NC=C2)C2=C(C(C=CC(C)=C2)=C2O)N=N1 CNJJEBORDAHQLN-CYBMUJFWSA-N 0.000 claims description 22
• 239000000126 substance Substances 0.000 claims description 22
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• 239000002243 precursor Substances 0.000 claims description 17
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• 206010053552 allodynia Diseases 0.000 claims description 13
• 201000011510 cancer Diseases 0.000 claims description 13
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• 208000015181 infectious disease Diseases 0.000 claims description 13
• 230000004054 inflammatory process Effects 0.000 claims description 13
• 208000019423 liver disease Diseases 0.000 claims description 13
• 208000030159 metabolic disease Diseases 0.000 claims description 13
• 208000016097 disease of metabolism Diseases 0.000 claims description 12
• 125000001845 4 membered carbocyclic group Chemical group 0.000 claims description 10
• 208000024827 Alzheimer disease Diseases 0.000 claims description 10
• 208000018737 Parkinson disease Diseases 0.000 claims description 10
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• 208000018501 Lymphatic disease Diseases 0.000 claims description 9
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• 229940079593 drug Drugs 0.000 claims description 9
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• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 208000022993 cryopyrin-associated periodic syndrome Diseases 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 208000002557 hidradenitis Diseases 0.000 claims description 8
• 201000007162 hidradenitis suppurativa Diseases 0.000 claims description 8
• 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims description 8
• 125000002837 carbocyclic group Chemical group 0.000 claims description 6
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
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• 230000020763 muscle atrophy Effects 0.000 claims description 2
• 201000000585 muscular atrophy Diseases 0.000 claims description 2
• 230000001105 regulatory effect Effects 0.000 claims 1
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• 108090000623 proteins and genes Proteins 0.000 abstract description 3
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• 229960003742 phenol Drugs 0.000 description 138
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 106
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 99
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 97
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 86
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
• 238000006243 chemical reaction Methods 0.000 description 77
• 239000002585 base Substances 0.000 description 67
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
• 238000005481 NMR spectroscopy Methods 0.000 description 50
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• 229910052796 boron Inorganic materials 0.000 description 45
• 229910001868 water Inorganic materials 0.000 description 43
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
• 235000019439 ethyl acetate Nutrition 0.000 description 37
• 238000003786 synthesis reaction Methods 0.000 description 36
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 35
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• 230000000694 effects Effects 0.000 description 32
• 125000003545 alkoxy group Chemical group 0.000 description 31
• 239000000243 solution Substances 0.000 description 31
• 238000001727 in vivo Methods 0.000 description 30
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 30
• 230000015572 biosynthetic process Effects 0.000 description 29
• 125000001424 substituent group Chemical group 0.000 description 29
• 230000002829 reductive effect Effects 0.000 description 27
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 26
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 24
• 239000012299 nitrogen atmosphere Substances 0.000 description 24
• 125000003118 aryl group Chemical group 0.000 description 23
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• 125000001309 chloro group Chemical group Cl* 0.000 description 22
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 22
• 238000000338 in vitro Methods 0.000 description 22
• 230000000155 isotopic effect Effects 0.000 description 22
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 22
• 239000007787 solid Substances 0.000 description 22
• 150000001412 amines Chemical class 0.000 description 21
• 238000002953 preparative HPLC Methods 0.000 description 21
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• 239000007864 aqueous solution Substances 0.000 description 20
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• 210000004556 brain Anatomy 0.000 description 19
• 239000000460 chlorine Substances 0.000 description 19
• 239000011734 sodium Substances 0.000 description 19
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
• 125000003277 amino group Chemical group 0.000 description 18
• 238000003818 flash chromatography Methods 0.000 description 18
• 239000001257 hydrogen Substances 0.000 description 18
• 238000003556 assay Methods 0.000 description 17
• 125000001072 heteroaryl group Chemical group 0.000 description 17
• 239000000546 pharmaceutical excipient Substances 0.000 description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 15
• 125000003342 alkenyl group Chemical group 0.000 description 15
• 125000000304 alkynyl group Chemical group 0.000 description 15
• 239000003085 diluting agent Substances 0.000 description 15
• 235000019253 formic acid Nutrition 0.000 description 15
• CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 14
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
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• OCHYNBAKUWJJOI-ZDUSSCGKSA-N CN1C[C@H](CNC2=C(C=NC=C3)C3=C(C(C=CC(C(F)(F)F)=C3)=C3O)N=N2)OCC1 Chemical compound CN1C[C@H](CNC2=C(C=NC=C3)C3=C(C(C=CC(C(F)(F)F)=C3)=C3O)N=N2)OCC1 OCHYNBAKUWJJOI-ZDUSSCGKSA-N 0.000 description 13
• 229920000858 Cyclodextrin Polymers 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
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• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
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• BYIOSXZLWBGZEP-INIZCTEOSA-N CC(C)(COC1)[C@H]1NC1=C(C=NC=C2)C2=C(C(C=CC(Cl)=C2)=C2O)N=N1 Chemical compound CC(C)(COC1)[C@H]1NC1=C(C=NC=C2)C2=C(C(C=CC(Cl)=C2)=C2O)N=N1 BYIOSXZLWBGZEP-INIZCTEOSA-N 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
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• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
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• 125000004093 cyano group Chemical group *C#N 0.000 description 8
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 8
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• AQVVPGZHVBQCFZ-UHFFFAOYSA-N 1-(4-chloro-2-methoxyphenyl)-3H-pyrido[3,4-d]pyridazin-4-one Chemical compound COC(C=C(C=C1)Cl)=C1C(N=N1)=C(C=CN=C2)C2=C1O AQVVPGZHVBQCFZ-UHFFFAOYSA-N 0.000 description 7
• XCJVXLDIKDCRLT-UHFFFAOYSA-N 4-chloro-1-(4-chloro-2-methoxyphenyl)pyrido[3,4-d]pyridazine Chemical compound COC(C=C(C=C1)Cl)=C1C(N=N1)=C(C=CN=C2)C2=C1Cl XCJVXLDIKDCRLT-UHFFFAOYSA-N 0.000 description 7
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• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
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• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 6
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