TWI801388B - 二氮雜雙環經取代之咪唑并嘧啶類及其用途 - Google Patents

Info

Publication number

TWI801388B

TWI801388B TW107120117A TW107120117A TWI801388B TW I801388 B TWI801388 B TW I801388B TW 107120117 A TW107120117 A TW 107120117A TW 107120117 A TW107120117 A TW 107120117A TW I801388 B TWI801388 B TW I801388B

Authority

TW

Taiwan

Prior art keywords

formula

compound

group

fluorine

methyl

Prior art date

2017-06-14

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• 150000005237 imidazopyrimidines Chemical class 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 107
• 238000011282 treatment Methods 0.000 claims abstract description 49
• 208000023504 respiratory system disease Diseases 0.000 claims abstract description 23
• 230000002265 prevention Effects 0.000 claims abstract description 21
• 239000003814 drug Substances 0.000 claims abstract description 17
• 206010041235 Snoring Diseases 0.000 claims abstract description 16
• 238000002360 preparation method Methods 0.000 claims abstract description 16
• 150000001875 compounds Chemical class 0.000 claims description 227
• -1 cyclobutyloxy, oxetan Chemical compound 0.000 claims description 111
• 150000003839 salts Chemical class 0.000 claims description 66
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 229910052731 fluorine Inorganic materials 0.000 claims description 49
• 239000011737 fluorine Substances 0.000 claims description 49
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 41
• 239000000460 chlorine Substances 0.000 claims description 40
• 229910052801 chlorine Inorganic materials 0.000 claims description 39
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 38
• 150000002431 hydrogen Chemical class 0.000 claims description 35
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 32
• 208000035475 disorder Diseases 0.000 claims description 30
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 27
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
• 229910052794 bromium Inorganic materials 0.000 claims description 27
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 23
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 22
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
• 125000001153 fluoro group Chemical group F* 0.000 claims description 17
• 208000001797 obstructive sleep apnea Diseases 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 201000010099 disease Diseases 0.000 claims description 16
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 15
• 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 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 125000004122 cyclic group Chemical group 0.000 claims description 11
• 208000003417 Central Sleep Apnea Diseases 0.000 claims description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000006239 protecting group Chemical group 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 7
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000003943 azolyl group Chemical group 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 206010003119 arrhythmia Diseases 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 6
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 230000001703 neuroimmune Effects 0.000 claims description 5
• 229940044551 receptor antagonist Drugs 0.000 claims description 5
• 239000002464 receptor antagonist Substances 0.000 claims description 5
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
• 229960002748 norepinephrine Drugs 0.000 claims description 4
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 229940123445 Tricyclic antidepressant Drugs 0.000 claims description 3
• 230000004913 activation Effects 0.000 claims description 3
• 125000006242 amine protecting group Chemical group 0.000 claims description 3
• 239000000935 antidepressant agent Substances 0.000 claims description 3
• 229940005513 antidepressants Drugs 0.000 claims description 3
• XNRHTMDHGDWBGP-UHFFFAOYSA-N carbamic acid;hydrochloride Chemical compound Cl.NC(O)=O XNRHTMDHGDWBGP-UHFFFAOYSA-N 0.000 claims description 3
• 239000003638 chemical reducing agent Substances 0.000 claims description 3
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
• 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 claims description 3
• 229940127089 cytotoxic agent Drugs 0.000 claims description 3
• 239000002254 cytotoxic agent Substances 0.000 claims description 3
• 231100000599 cytotoxic agent Toxicity 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 239000003018 immunosuppressive agent Substances 0.000 claims description 3
• 239000012948 isocyanate Substances 0.000 claims description 3
• 150000002513 isocyanates Chemical class 0.000 claims description 3
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
• 231100000252 nontoxic Toxicity 0.000 claims description 3
• 230000003000 nontoxic effect Effects 0.000 claims description 3
• 239000003169 respiratory stimulant agent Substances 0.000 claims description 3
• 229940066293 respiratory stimulants Drugs 0.000 claims description 3
• 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 3
• 239000000021 stimulant Substances 0.000 claims description 3
• 239000003029 tricyclic antidepressant agent Substances 0.000 claims description 3
• VDKJCAWGDJJKNL-UHFFFAOYSA-N (3-chloro-6-methoxypyridin-2-yl)-[3-[[2-(4-propan-2-ylphenyl)imidazo[1,2-a]pyrimidin-3-yl]methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical group ClC=1C(=NC(=CC=1)OC)C(=O)N1C2CN(CC1CC2)CC1=C(N=C2N1C=CC=N2)C1=CC=C(C=C1)C(C)C VDKJCAWGDJJKNL-UHFFFAOYSA-N 0.000 claims description 2
• OGGHXOJOVOYBOH-UHFFFAOYSA-N (3-fluoro-6-methoxypyridin-2-yl)-[3-[[2-(4-propan-2-ylphenyl)imidazo[1,2-a]pyrimidin-3-yl]methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical group FC=1C(=NC(=CC=1)OC)C(=O)N1C2CN(CC1CC2)CC1=C(N=C2N1C=CC=N2)C1=CC=C(C=C1)C(C)C OGGHXOJOVOYBOH-UHFFFAOYSA-N 0.000 claims description 2
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
• 239000000470 constituent Substances 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 239000002955 immunomodulating agent Substances 0.000 claims description 2
• 229940121354 immunomodulator Drugs 0.000 claims description 2
• 229960003444 immunosuppressant agent Drugs 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 229940127296 soluble guanylate cyclase stimulator Drugs 0.000 claims description 2
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
• 208000036110 Neuroinflammatory disease Diseases 0.000 claims 3
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
• 150000001263 acyl chlorides Chemical class 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• 230000000414 obstructive effect Effects 0.000 abstract description 9
• 230000006806 disease prevention Effects 0.000 abstract description 5
• 230000008569 process Effects 0.000 abstract description 4
• 150000005238 imidazo[1,2-a]pyrimidines Chemical class 0.000 abstract description 3
• 206010040978 Sleep apnoeas Diseases 0.000 abstract 2
• 239000000203 mixture Substances 0.000 description 76
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 58
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 46
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
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• 239000012453 solvate Substances 0.000 description 41
• 239000000243 solution Substances 0.000 description 40
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• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 34
• 238000005160 1H NMR spectroscopy Methods 0.000 description 32
• 238000003756 stirring Methods 0.000 description 32
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
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• 101001050878 Homo sapiens Potassium channel subfamily K member 9 Proteins 0.000 description 25
• 239000000126 substance Substances 0.000 description 25
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• 238000002953 preparative HPLC Methods 0.000 description 22
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• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 20
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• 238000000825 ultraviolet detection Methods 0.000 description 17
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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 16
• 102100024986 Potassium channel subfamily K member 9 Human genes 0.000 description 16
• 239000002585 base Substances 0.000 description 16
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• 239000005557 antagonist Substances 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
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• 230000000694 effects Effects 0.000 description 11
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• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
• 230000000241 respiratory effect Effects 0.000 description 11
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 10
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• 150000001335 aliphatic alkanes Chemical class 0.000 description 10
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• 238000005481 NMR spectroscopy Methods 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 210000004027 cell Anatomy 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• 238000012360 testing method Methods 0.000 description 9
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• 239000002253 acid Substances 0.000 description 8
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• 235000019341 magnesium sulphate Nutrition 0.000 description 8
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
• 241000282887 Suidae Species 0.000 description 7
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• 230000001684 chronic effect Effects 0.000 description 7
• 210000002216 heart Anatomy 0.000 description 7
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• 238000000926 separation method Methods 0.000 description 7
• UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
• 208000011580 syndromic disease Diseases 0.000 description 7
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• 238000004440 column chromatography Methods 0.000 description 6
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