JP5543068B2 - キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 - Google Patents
キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 Download PDFInfo
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- JP5543068B2 JP5543068B2 JP2007549590A JP2007549590A JP5543068B2 JP 5543068 B2 JP5543068 B2 JP 5543068B2 JP 2007549590 A JP2007549590 A JP 2007549590A JP 2007549590 A JP2007549590 A JP 2007549590A JP 5543068 B2 JP5543068 B2 JP 5543068B2
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- alkyl
- heteroaryl
- aryl
- heterocyclyl
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- 150000001923 cyclic compounds Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 316
- 150000001875 compounds Chemical class 0.000 claims description 278
- 125000003118 aryl group Chemical group 0.000 claims description 244
- 125000000623 heterocyclic group Chemical group 0.000 claims description 228
- 125000001072 heteroaryl group Chemical group 0.000 claims description 220
- 125000001424 substituent group Chemical group 0.000 claims description 202
- 125000003545 alkoxy group Chemical group 0.000 claims description 145
- 125000003342 alkenyl group Chemical group 0.000 claims description 140
- 125000002947 alkylene group Chemical group 0.000 claims description 137
- -1 arylalkylenyl Chemical group 0.000 claims description 124
- 125000000304 alkynyl group Chemical group 0.000 claims description 118
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 106
- 150000003839 salts Chemical class 0.000 claims description 98
- 229910052736 halogen Inorganic materials 0.000 claims description 90
- 125000004450 alkenylene group Chemical group 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 239000001257 hydrogen Substances 0.000 claims description 82
- 229910052799 carbon Inorganic materials 0.000 claims description 71
- 150000002367 halogens Chemical class 0.000 claims description 66
- 125000005843 halogen group Chemical group 0.000 claims description 60
- 125000001188 haloalkyl group Chemical group 0.000 claims description 59
- 125000005466 alkylenyl group Chemical group 0.000 claims description 55
- 125000005842 heteroatom Chemical group 0.000 claims description 54
- 150000002431 hydrogen Chemical class 0.000 claims description 52
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
- 125000004104 aryloxy group Chemical group 0.000 claims description 42
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 41
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 41
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 41
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 38
- 229920006395 saturated elastomer Polymers 0.000 claims description 34
- 125000004414 alkyl thio group Chemical group 0.000 claims description 33
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 125000004419 alkynylene group Chemical group 0.000 claims description 30
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 24
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 22
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 22
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 22
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 22
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 22
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000000732 arylene group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000005549 heteroarylene group Chemical group 0.000 claims description 19
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 18
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 18
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- 125000004423 acyloxy group Chemical group 0.000 claims description 14
- 125000001589 carboacyl group Chemical group 0.000 claims description 14
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000005110 aryl thio group Chemical group 0.000 claims description 12
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000002256 xylenyl group Chemical group C1(C(C=CC=C1)C)(C)* 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 252
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
- 239000000243 solution Substances 0.000 description 165
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 112
- 239000011541 reaction mixture Substances 0.000 description 111
- 230000002829 reductive effect Effects 0.000 description 109
- 239000007787 solid Substances 0.000 description 94
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 77
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
- 239000002904 solvent Substances 0.000 description 73
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 70
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 69
- 229910004298 SiO 2 Inorganic materials 0.000 description 63
- 238000004587 chromatography analysis Methods 0.000 description 63
- 238000000034 method Methods 0.000 description 60
- 239000011734 sodium Substances 0.000 description 54
- 239000012267 brine Substances 0.000 description 47
- 239000010410 layer Substances 0.000 description 47
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 150000001721 carbon Chemical group 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 229910052720 vanadium Inorganic materials 0.000 description 39
- 235000019439 ethyl acetate Nutrition 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 229910052757 nitrogen Inorganic materials 0.000 description 34
- 241001465754 Metazoa Species 0.000 description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
- 239000000706 filtrate Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 102000004127 Cytokines Human genes 0.000 description 25
- 108090000695 Cytokines Proteins 0.000 description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 23
- 239000006188 syrup Substances 0.000 description 23
- 235000020357 syrup Nutrition 0.000 description 23
- 238000010992 reflux Methods 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 201000010099 disease Diseases 0.000 description 21
- 239000006260 foam Substances 0.000 description 21
- 229910052717 sulfur Inorganic materials 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical group C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 18
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 18
- 238000002425 crystallisation Methods 0.000 description 17
- 230000008025 crystallization Effects 0.000 description 17
- 239000000543 intermediate Substances 0.000 description 17
- 239000000651 prodrug Substances 0.000 description 17
- 229940002612 prodrug Drugs 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000843 powder Substances 0.000 description 15
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 14
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 125000004076 pyridyl group Chemical group 0.000 description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 150000001414 amino alcohols Chemical class 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 125000003386 piperidinyl group Chemical group 0.000 description 13
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- YHEPBWTXCZVUHG-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-6-amine Chemical compound N1=C2C(N)=CC=CC2=C2NC=NC2=C1 YHEPBWTXCZVUHG-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000007796 conventional method Methods 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 125000003396 thiol group Chemical class [H]S* 0.000 description 11
- 230000003612 virological effect Effects 0.000 description 11
- IDUUCDZKSKUCOP-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C(NC=N3)C3=CN=C21 IDUUCDZKSKUCOP-UHFFFAOYSA-N 0.000 description 10
- ZRFUZDDJSQVQBY-UHFFFAOYSA-N 4-chloro-3-nitroquinoline Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CN=C21 ZRFUZDDJSQVQBY-UHFFFAOYSA-N 0.000 description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 230000028993 immune response Effects 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 125000002757 morpholinyl group Chemical group 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000010189 synthetic method Methods 0.000 description 10
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 10
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 9
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 9
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 239000000908 ammonium hydroxide Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 230000001613 neoplastic effect Effects 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 7
- FDOIXMGDTOEUQL-UHFFFAOYSA-N 4-chloro-3-nitro-1,5-naphthyridine Chemical compound C1=CC=NC2=C(Cl)C([N+](=O)[O-])=CN=C21 FDOIXMGDTOEUQL-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 230000002452 interceptive effect Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- IEIGFDMBSIRMEW-UHFFFAOYSA-N 3-chloro-4-nitroquinoline Chemical compound C1=CC=C2C([N+](=O)[O-])=C(Cl)C=NC2=C1 IEIGFDMBSIRMEW-UHFFFAOYSA-N 0.000 description 6
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 241000700605 Viruses Species 0.000 description 6
- 229940024606 amino acid Drugs 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
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- 238000001953 recrystallisation Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 6
- 125000001984 thiazolidinyl group Chemical group 0.000 description 6
- BKMMTJMQCTUHRP-VKHMYHEASA-N (S)-2-aminopropan-1-ol Chemical compound C[C@H](N)CO BKMMTJMQCTUHRP-VKHMYHEASA-N 0.000 description 5
- MIDQVYLLSDOPIL-UHFFFAOYSA-N 1,5-naphthyridine-3,4-diamine Chemical compound C1=CC=NC2=C(N)C(N)=CN=C21 MIDQVYLLSDOPIL-UHFFFAOYSA-N 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- BGWMHFKCAUBYJJ-UHFFFAOYSA-N ethyl 2-chloroethanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CCl BGWMHFKCAUBYJJ-UHFFFAOYSA-N 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 230000006698 induction Effects 0.000 description 5
- 230000001939 inductive effect Effects 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- 125000002971 oxazolyl group Chemical group 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 125000006513 pyridinyl methyl group Chemical group 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
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- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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| US64061404P | 2004-12-30 | 2004-12-30 | |
| US60/640,614 | 2004-12-30 | ||
| US69725705P | 2005-07-07 | 2005-07-07 | |
| US60/697,257 | 2005-07-07 | ||
| PCT/US2005/047258 WO2006074003A2 (en) | 2004-12-30 | 2005-12-29 | CHIRAL FUSED [1,2]IMIDAZO[4,5-c] RING COMPOUNDS |
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| JP2008526754A JP2008526754A (ja) | 2008-07-24 |
| JP2008526754A5 JP2008526754A5 (OSRAM) | 2009-02-19 |
| JP5543068B2 true JP5543068B2 (ja) | 2014-07-09 |
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| US (3) | US7943609B2 (OSRAM) |
| EP (1) | EP1831226B1 (OSRAM) |
| JP (1) | JP5543068B2 (OSRAM) |
| AU (1) | AU2005322898B2 (OSRAM) |
| CA (1) | CA2592904C (OSRAM) |
| ES (1) | ES2392647T3 (OSRAM) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH078366B2 (ja) | 1986-10-03 | 1995-02-01 | 株式会社クボタ | 熱間圧延用溶接肉盛ロ−ル |
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2005
- 2005-12-29 AU AU2005322898A patent/AU2005322898B2/en not_active Ceased
- 2005-12-29 JP JP2007549590A patent/JP5543068B2/ja not_active Expired - Fee Related
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH078366B2 (ja) | 1986-10-03 | 1995-02-01 | 株式会社クボタ | 熱間圧延用溶接肉盛ロ−ル |
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| US20110207725A1 (en) | 2011-08-25 |
| CA2592904A1 (en) | 2006-07-13 |
| EP1831226A2 (en) | 2007-09-12 |
| CA2592904C (en) | 2015-04-07 |
| WO2006074003A2 (en) | 2006-07-13 |
| US20080269192A1 (en) | 2008-10-30 |
| EP1831226B1 (en) | 2012-08-08 |
| WO2006074003A3 (en) | 2007-11-22 |
| US8207162B2 (en) | 2012-06-26 |
| AU2005322898B2 (en) | 2011-11-24 |
| AU2005322898A1 (en) | 2006-07-13 |
| EP1831226A4 (en) | 2008-11-05 |
| US7943609B2 (en) | 2011-05-17 |
| US8546383B2 (en) | 2013-10-01 |
| US20120232057A1 (en) | 2012-09-13 |
| ES2392647T3 (es) | 2012-12-12 |
| JP2008526754A (ja) | 2008-07-24 |
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