JP5847193B2 - フラビウイルス科ウイルスの大環状インヒビター - Google Patents

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Publication number

JP5847193B2

JP5847193B2 JP2013543356A JP2013543356A JP5847193B2 JP 5847193 B2 JP5847193 B2 JP 5847193B2 JP 2013543356 A JP2013543356 A JP 2013543356A JP 2013543356 A JP2013543356 A JP 2013543356A JP 5847193 B2 JP5847193 B2 JP 5847193B2

Authority

JP

Japan

Prior art keywords

optionally substituted

alkyl

mmol

aryl

another aspect

Prior art date

2010-12-10

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.)

Expired - Fee Related

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• 239000003112 inhibitor Substances 0.000 title claims description 75
• 241000710781 Flaviviridae Species 0.000 title description 13
• 150000001875 compounds Chemical class 0.000 claims description 254
• -1 substituted Chemical class 0.000 claims description 189
• 239000000203 mixture Substances 0.000 claims description 111
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 87
• 125000000623 heterocyclic group Chemical group 0.000 claims description 85
• 125000002947 alkylene group Chemical group 0.000 claims description 77
• 125000000217 alkyl group Chemical group 0.000 claims description 64
• 125000004450 alkenylene group Chemical group 0.000 claims description 57
• 125000003107 substituted aryl group Chemical group 0.000 claims description 47
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 241000711549 Hepacivirus C Species 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 42
• 125000004419 alkynylene group Chemical group 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 38
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 36
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 35
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 238000000034 method Methods 0.000 claims description 31
• 229910052799 carbon Inorganic materials 0.000 claims description 30
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 27
• 239000002777 nucleoside Substances 0.000 claims description 27
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• 125000000304 alkynyl group Chemical group 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 239000003814 drug Substances 0.000 claims description 21
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• 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 16
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 15
• 125000000732 arylene group Chemical group 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 108010050904 Interferons Proteins 0.000 claims description 14
• 102000014150 Interferons Human genes 0.000 claims description 14
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• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 229940079322 interferon Drugs 0.000 claims description 11
• 239000002773 nucleotide Substances 0.000 claims description 11
• 125000003729 nucleotide group Chemical group 0.000 claims description 11
• 229960000329 ribavirin Drugs 0.000 claims description 11
• 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 11
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 10
• 125000006557 (C2-C5) alkylene group Chemical group 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
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• 125000005549 heteroarylene group Chemical group 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
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• 239000003937 drug carrier Substances 0.000 claims description 7
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• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
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• 235000019439 ethyl acetate Nutrition 0.000 description 134
• 239000000243 solution Substances 0.000 description 131
• 238000005481 NMR spectroscopy Methods 0.000 description 108
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• 238000006243 chemical reaction Methods 0.000 description 103
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 98
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 81
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• 239000007787 solid Substances 0.000 description 62
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
• 239000003921 oil Substances 0.000 description 51
• 235000019198 oils Nutrition 0.000 description 50
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 49
• 229910052757 nitrogen Inorganic materials 0.000 description 49
• 125000004432 carbon atom Chemical group C* 0.000 description 48
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 42
• 239000000047 product Substances 0.000 description 41
• 239000004480 active ingredient Substances 0.000 description 40
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• 238000010898 silica gel chromatography Methods 0.000 description 37
• 239000002904 solvent Substances 0.000 description 36
• 229910004298 SiO 2 Inorganic materials 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
• 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 description 30
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 26
• 150000002148 esters Chemical class 0.000 description 25
• 210000004027 cell Anatomy 0.000 description 23
• 239000011734 sodium Substances 0.000 description 23
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
• 150000001721 carbon Chemical group 0.000 description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 21
• 239000010410 layer Substances 0.000 description 21
• 239000012044 organic layer Substances 0.000 description 21
• 239000000741 silica gel Substances 0.000 description 21
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• 239000003039 volatile agent Substances 0.000 description 19
• 239000000284 extract Substances 0.000 description 18
• 238000003818 flash chromatography Methods 0.000 description 18
• 239000012299 nitrogen atmosphere Substances 0.000 description 17
• 125000006239 protecting group Chemical group 0.000 description 17
• PRXGMEURJXGKOP-UHFFFAOYSA-N NP(N)=O Chemical class NP(N)=O PRXGMEURJXGKOP-UHFFFAOYSA-N 0.000 description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
• 238000000746 purification Methods 0.000 description 16
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 15
• 239000013543 active substance Substances 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 14
• 230000002209 hydrophobic effect Effects 0.000 description 14
• 239000000377 silicon dioxide Substances 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• 239000006260 foam Substances 0.000 description 13
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• 238000010992 reflux Methods 0.000 description 13
• 238000012360 testing method Methods 0.000 description 13
• 238000011282 treatment Methods 0.000 description 13
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• 239000012298 atmosphere Substances 0.000 description 12
• 230000000694 effects Effects 0.000 description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
• 239000007788 liquid Substances 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
• 125000003710 aryl alkyl group Chemical group 0.000 description 11
• 238000003556 assay Methods 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• 238000002360 preparation method Methods 0.000 description 11
• 239000003826 tablet Substances 0.000 description 11
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
• 230000000840 anti-viral effect Effects 0.000 description 10
• 125000001072 heteroaryl group Chemical group 0.000 description 10
• 230000005764 inhibitory process Effects 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 10
• HJUAUQYSCWRRHQ-HTQZYQBOSA-N (2r,3r)-3-methoxy-2-methylhept-6-enoic acid Chemical compound OC(=O)[C@H](C)[C@H](OC)CCC=C HJUAUQYSCWRRHQ-HTQZYQBOSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 241000400611 Eucalyptus deanei Species 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
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• 125000005843 halogen group Chemical group 0.000 description 9
• 229910052739 hydrogen Inorganic materials 0.000 description 9
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound 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 9
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