JP6122868B2 - 抗ウイルス剤としてのピラゾロ［１，５−ａ］ピリミジン - Google Patents

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Publication number

JP6122868B2

JP6122868B2 JP2014548913A JP2014548913A JP6122868B2 JP 6122868 B2 JP6122868 B2 JP 6122868B2 JP 2014548913 A JP2014548913 A JP 2014548913A JP 2014548913 A JP2014548913 A JP 2014548913A JP 6122868 B2 JP6122868 B2 JP 6122868B2

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JP

Japan

Prior art keywords

compound

formula

alkyl

pharmaceutically acceptable

nhr

Prior art date

2011-12-22

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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• 239000003443 antiviral agent Substances 0.000 title description 2
• LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 466
• 239000000203 mixture Substances 0.000 claims description 176
• 150000003839 salts Chemical class 0.000 claims description 175
• -1 1,2,3,4-tetrahydronaphthyl Chemical group 0.000 claims description 106
• 239000003814 drug Substances 0.000 claims description 98
• 241000711902 Pneumovirus Species 0.000 claims description 97
• 125000000623 heterocyclic group Chemical group 0.000 claims description 91
• 238000011282 treatment Methods 0.000 claims description 85
• 230000009385 viral infection Effects 0.000 claims description 78
• 229910052799 carbon Inorganic materials 0.000 claims description 77
• 125000003118 aryl group Chemical group 0.000 claims description 65
• 241000124008 Mammalia Species 0.000 claims description 61
• 125000000217 alkyl group Chemical group 0.000 claims description 58
• 241000700605 Viruses Species 0.000 claims description 56
• 229940124597 therapeutic agent Drugs 0.000 claims description 53
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 46
• 125000004432 carbon atom Chemical group C* 0.000 claims description 45
• 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 44
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 42
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 41
• 239000008194 pharmaceutical composition Substances 0.000 claims description 38
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• 150000002367 halogens Chemical class 0.000 claims description 37
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 150000001721 carbon Chemical group 0.000 claims description 25
• 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 22
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 22
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000004043 oxo group Chemical group O=* 0.000 claims description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
• 230000001225 therapeutic effect Effects 0.000 claims description 15
• 125000001624 naphthyl group Chemical group 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 239000003795 chemical substances by application Substances 0.000 claims description 11
• 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 9
• 229960000329 ribavirin Drugs 0.000 claims description 9
• HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 8
• 125000001188 haloalkyl group Chemical group 0.000 claims description 8
• 229960000402 palivizumab Drugs 0.000 claims description 8
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 108700002314 gontivimab Proteins 0.000 claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims description 7
• 125000001041 indolyl group Chemical group 0.000 claims description 7
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 7
• 238000013160 medical therapy Methods 0.000 claims description 7
• 229960001521 motavizumab Drugs 0.000 claims description 7
• 125000005493 quinolyl group Chemical group 0.000 claims description 7
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
• BLUJRJMLDHEMRX-UHFFFAOYSA-N 2-[[2-hydroxy-5-[(5-methyltetrazol-1-yl)iminomethyl]phenyl]-(4-hydroxyphenyl)methyl]-4-[(5-methyltetrazol-1-yl)iminomethyl]phenol Chemical compound Cc1nnnn1N=Cc1ccc(O)c(c1)C(c1ccc(O)cc1)c1cc(C=Nn2nnnc2C)ccc1O BLUJRJMLDHEMRX-UHFFFAOYSA-N 0.000 claims description 5
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 238000011321 prophylaxis Methods 0.000 claims description 4
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 4
• IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims description 2
• 241000257303 Hymenoptera Species 0.000 claims 1
• 150000002148 esters Chemical class 0.000 description 132
• 238000000034 method Methods 0.000 description 118
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 116
• 239000000543 intermediate Substances 0.000 description 103
• 208000015181 infectious disease Diseases 0.000 description 89
• 239000000243 solution Substances 0.000 description 65
• 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 description 63
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 50
• 239000011541 reaction mixture Substances 0.000 description 49
• 239000004480 active ingredient Substances 0.000 description 46
• 235000019439 ethyl acetate Nutrition 0.000 description 45
• 238000009472 formulation Methods 0.000 description 44
• 238000002360 preparation method Methods 0.000 description 44
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 41
• 229940079593 drug Drugs 0.000 description 37
• 210000004027 cell Anatomy 0.000 description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• 0 Cc1c[n]2nc(C(CCCC3)*3C(c3nccc(-c4ccccc4)c3)=O)cc2nc1N(C[C@]1C#N)C[C@@]1O Chemical compound Cc1c[n]2nc(C(CCCC3)*3C(c3nccc(-c4ccccc4)c3)=O)cc2nc1N(C[C@]1C#N)C[C@@]1O 0.000 description 32
• 125000001424 substituent group Chemical group 0.000 description 32
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 31
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 31
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 30
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 30
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 29
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 28
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 28
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 28
• 230000002829 reductive effect Effects 0.000 description 23
• 239000000843 powder Substances 0.000 description 21
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• 230000002458 infectious effect Effects 0.000 description 20
• 239000002245 particle Substances 0.000 description 19
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
• 239000000546 pharmaceutical excipient Substances 0.000 description 18
• 239000000047 product Substances 0.000 description 18
• 208000036142 Viral infection Diseases 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 16
• 230000000694 effects Effects 0.000 description 16
• 229940002612 prodrug Drugs 0.000 description 16
• 239000000651 prodrug Substances 0.000 description 16
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 16
• 239000012267 brine Substances 0.000 description 15
• 238000004128 high performance liquid chromatography Methods 0.000 description 15
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 15
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 15
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 14
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 14
• AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 14
• MJQSRSOTRPMVKB-UHFFFAOYSA-N 5h-imidazo[4,5-c]pyridazine Chemical compound C1=NNC2=NC=NC2=C1 MJQSRSOTRPMVKB-UHFFFAOYSA-N 0.000 description 14
• 239000000443 aerosol Substances 0.000 description 14
• 125000003545 alkoxy group Chemical group 0.000 description 14
• 239000012453 solvate Substances 0.000 description 14
• YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 14
• 238000005481 NMR spectroscopy Methods 0.000 description 13
• 230000000840 anti-viral effect Effects 0.000 description 13
• 125000004429 atom Chemical group 0.000 description 13
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• BLUGYPPOFIHFJS-UUFHNPECSA-N (2s)-n-[(2s)-1-[[(3r,4s,5s)-3-methoxy-1-[(2s)-2-[(1r,2r)-1-methoxy-2-methyl-3-oxo-3-[[(1s)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methyl-2-(methylamino)butanamid Chemical compound CN[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C=1SC=CN=1)CC1=CC=CC=C1 BLUGYPPOFIHFJS-UUFHNPECSA-N 0.000 description 11
• 208000007934 ACTH-independent macronodular adrenal hyperplasia Diseases 0.000 description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
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• 229910052786 argon Inorganic materials 0.000 description 9
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• DATJETPTDKFEEF-UHFFFAOYSA-N pyrrolidine-3-carbonitrile Chemical compound N#CC1CCNC1 DATJETPTDKFEEF-UHFFFAOYSA-N 0.000 description 9
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• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
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• 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 4
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