JP6896113B2 - ジアザ二環式置換イミダゾピリミジンおよび呼吸障害を治療するためのその使用 - Google Patents

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Publication number

JP6896113B2

JP6896113B2 JP2019569416A JP2019569416A JP6896113B2 JP 6896113 B2 JP6896113 B2 JP 6896113B2 JP 2019569416 A JP2019569416 A JP 2019569416A JP 2019569416 A JP2019569416 A JP 2019569416A JP 6896113 B2 JP6896113 B2 JP 6896113B2

Authority

JP

Japan

Prior art keywords

formula

fluorine

compound

methyl

group

Prior art date

2017-06-14

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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• 208000023504 respiratory system disease Diseases 0.000 title claims description 12
• 238000006467 substitution reaction Methods 0.000 title description 3
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 217
• -1 cyclobutyloxy, oxetane-3-yloxy, tetrahydrofuran-3-yloxy, tetrahydro-2H-pyran-4-yloxy Chemical group 0.000 claims description 178
• 238000000034 method Methods 0.000 claims description 109
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 86
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
• 150000003839 salts Chemical class 0.000 claims description 55
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 54
• 229910052731 fluorine Inorganic materials 0.000 claims description 50
• 239000011737 fluorine Substances 0.000 claims description 50
• 239000012453 solvate Substances 0.000 claims description 49
• 238000006243 chemical reaction Methods 0.000 claims description 43
• 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
• 208000035475 disorder Diseases 0.000 claims description 40
• HJCFDCKEUGZLPS-UHFFFAOYSA-N 2-(4-chlorophenyl)-1h-imidazole Chemical compound C1=CC(Cl)=CC=C1C1=NC=CN1 HJCFDCKEUGZLPS-UHFFFAOYSA-N 0.000 claims description 39
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 39
• 229910052801 chlorine Inorganic materials 0.000 claims description 39
• 150000002431 hydrogen Chemical class 0.000 claims description 33
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 30
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
• 239000002904 solvent Substances 0.000 claims description 26
• 150000002460 imidazoles Chemical class 0.000 claims description 22
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 21
• 125000001153 fluoro group Chemical group F* 0.000 claims description 20
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
• 208000001797 obstructive sleep apnea Diseases 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 230000000241 respiratory effect Effects 0.000 claims description 14
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 13
• 230000014509 gene expression Effects 0.000 claims description 13
• 230000007958 sleep Effects 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
• 125000006239 protecting group Chemical group 0.000 claims description 12
• 206010041235 Snoring Diseases 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 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 10
• 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
• 239000002253 acid Substances 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 206010003119 arrhythmia Diseases 0.000 claims description 5
• 230000006793 arrhythmia Effects 0.000 claims description 5
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
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• 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 5
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group 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
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
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• 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
• 229940127557 pharmaceutical product Drugs 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 229940044551 receptor antagonist Drugs 0.000 claims description 4
• 239000002464 receptor antagonist Substances 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
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 3
• 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 3
• 229940123445 Tricyclic antidepressant Drugs 0.000 claims description 3
• 230000004913 activation Effects 0.000 claims description 3
• 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 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
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 3
• 230000001703 neuroimmune Effects 0.000 claims description 3
• 231100000252 nontoxic Toxicity 0.000 claims description 3
• 230000003000 nontoxic effect Effects 0.000 claims description 3
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• 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 3
• 230000002295 serotoninergic effect Effects 0.000 claims description 3
• 239000000021 stimulant Substances 0.000 claims description 3
• 239000003029 tricyclic antidepressant agent Substances 0.000 claims description 3
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
• RKKUVFMSCLZKEV-UHFFFAOYSA-N 3-fluoro-6-methoxypyridine-2-carbaldehyde Chemical compound COC1=CC=C(F)C(C=O)=N1 RKKUVFMSCLZKEV-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
• 239000003638 chemical reducing agent Substances 0.000 claims description 2
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
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• 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
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
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• 239000000203 mixture Substances 0.000 description 76
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
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