AU2004315771A1 - Sulfone substituted imidazo ring ethers - Google Patents

Info

Publication number

AU2004315771A1

AU2004315771A1 AU2004315771A AU2004315771A AU2004315771A1 AU 2004315771 A1 AU2004315771 A1 AU 2004315771A1 AU 2004315771 A AU2004315771 A AU 2004315771A AU 2004315771 A AU2004315771 A AU 2004315771A AU 2004315771 A1 AU2004315771 A1 AU 2004315771A1

Authority

AU

Australia

Prior art keywords

group

alkyl

heterocyclyl

alkylenyl

heteroaryl

Prior art date

2003-12-04

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.)

Abandoned

Links

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• 150000002170 ethers Chemical class 0.000 title description 2
• 150000003457 sulfones Chemical group 0.000 title description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 398
• 125000005466 alkylenyl group Chemical group 0.000 claims description 276
• 125000000623 heterocyclic group Chemical group 0.000 claims description 235
• 125000001072 heteroaryl group Chemical group 0.000 claims description 201
• 125000003118 aryl group Chemical group 0.000 claims description 182
• 125000000304 alkynyl group Chemical group 0.000 claims description 153
• 125000003342 alkenyl group Chemical group 0.000 claims description 147
• 150000001875 compounds Chemical class 0.000 claims description 141
• 125000002947 alkylene group Chemical group 0.000 claims description 135
• -1 nitro, hydroxy Chemical group 0.000 claims description 126
• 125000003545 alkoxy group Chemical group 0.000 claims description 120
• 150000003839 salts Chemical class 0.000 claims description 118
• 229910052739 hydrogen Inorganic materials 0.000 claims description 117
• 125000004450 alkenylene group Chemical group 0.000 claims description 116
• 125000004419 alkynylene group Chemical group 0.000 claims description 116
• 239000001257 hydrogen Substances 0.000 claims description 112
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 86
• 125000001424 substituent group Chemical group 0.000 claims description 69
• 229910052736 halogen Inorganic materials 0.000 claims description 63
• 229910052799 carbon Inorganic materials 0.000 claims description 62
• 150000002367 halogens Chemical class 0.000 claims description 62
• 150000002431 hydrogen Chemical class 0.000 claims description 60
• 125000004432 carbon atom Chemical group C* 0.000 claims description 55
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 52
• 125000003282 alkyl amino group Chemical group 0.000 claims description 51
• 125000004104 aryloxy group Chemical group 0.000 claims description 51
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 51
• 125000000732 arylene group Chemical group 0.000 claims description 49
• 125000005549 heteroarylene group Chemical group 0.000 claims description 48
• 238000000034 method Methods 0.000 claims description 48
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 46
• 125000004043 oxo group Chemical group O=* 0.000 claims description 46
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
• 125000001188 haloalkyl group Chemical group 0.000 claims description 36
• 229920006395 saturated elastomer Polymers 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 31
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
• 125000001153 fluoro group Chemical group F* 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 102000004127 Cytokines Human genes 0.000 claims description 26
• 108090000695 Cytokines Proteins 0.000 claims description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 23
• 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 23
• 241001465754 Metazoa Species 0.000 claims description 22
• 201000010099 disease Diseases 0.000 claims description 22
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 22
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 230000015572 biosynthetic process Effects 0.000 claims description 14
• 230000002452 interceptive effect Effects 0.000 claims description 13
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 11
• 125000004414 alkyl thio group Chemical group 0.000 claims description 11
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 230000003612 virological effect Effects 0.000 claims description 10
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 9
• 230000001613 neoplastic effect Effects 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• XTEOJPUYZWEXFI-UHFFFAOYSA-N butyl n-[3-[4-(imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylcarbamate Chemical compound S1C(CC(C)C)=CC(C=2C=CC(CN3C=NC=C3)=CC=2)=C1S(=O)(=O)NC(=O)OCCCC XTEOJPUYZWEXFI-UHFFFAOYSA-N 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 230000001939 inductive effect Effects 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 241001091551 Clio Species 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 230000001419 dependent effect Effects 0.000 claims 7
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 4
• 241001286462 Caio Species 0.000 claims 2
• BPPVUXSMLBXYGG-UHFFFAOYSA-N 4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1h-pyrazol-3-one Chemical compound CC1=C(C(=O)C=2C(N(C)NC=2)=O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 BPPVUXSMLBXYGG-UHFFFAOYSA-N 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 358
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 198
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 129
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 125
• 238000006243 chemical reaction Methods 0.000 description 121
• 239000000243 solution Substances 0.000 description 109
• 239000007787 solid Substances 0.000 description 105
• 239000011541 reaction mixture Substances 0.000 description 100
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
• 239000000463 material Substances 0.000 description 95
• 239000000203 mixture Substances 0.000 description 78
• 239000003921 oil Substances 0.000 description 74
• 235000019198 oils Nutrition 0.000 description 74
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 65
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 61
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
• 239000000741 silica gel Substances 0.000 description 50
• 229910002027 silica gel Inorganic materials 0.000 description 50
• 238000001914 filtration Methods 0.000 description 49
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
• 239000012267 brine Substances 0.000 description 43
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 43
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
• 239000000047 product Substances 0.000 description 41
• 238000004458 analytical method Methods 0.000 description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• 239000007858 starting material Substances 0.000 description 37
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 36
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 33
• 238000005481 NMR spectroscopy Methods 0.000 description 32
• 239000012043 crude product Substances 0.000 description 32
• 239000000843 powder Substances 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
• 238000010992 reflux Methods 0.000 description 28
• 238000007796 conventional method Methods 0.000 description 26
• 239000006260 foam Substances 0.000 description 26
• 239000012044 organic layer Substances 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• 239000002904 solvent Substances 0.000 description 25
• 238000004440 column chromatography Methods 0.000 description 24
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 23
• 238000003818 flash chromatography Methods 0.000 description 23
• 239000000725 suspension Substances 0.000 description 23
• 238000004809 thin layer chromatography Methods 0.000 description 23
• 239000012312 sodium hydride Substances 0.000 description 22
• 229910000104 sodium hydride Inorganic materials 0.000 description 22
• 239000003795 chemical substances by application Substances 0.000 description 20
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 19
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
• 239000000706 filtrate Substances 0.000 description 18
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 18
• 229910000029 sodium carbonate Inorganic materials 0.000 description 18
• HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical class NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 description 17
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
• 150000001721 carbon Chemical group 0.000 description 17
• 239000013078 crystal Substances 0.000 description 17
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 16
• 238000004128 high performance liquid chromatography Methods 0.000 description 16
• 238000000746 purification Methods 0.000 description 16
• 239000010410 layer Substances 0.000 description 15
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 15
• WUIJTQZXUURFQU-UHFFFAOYSA-N 1-methylsulfonylethene Chemical compound CS(=O)(=O)C=C WUIJTQZXUURFQU-UHFFFAOYSA-N 0.000 description 14
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
• 239000002244 precipitate Substances 0.000 description 14
• ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 13
• 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 13
• 239000012299 nitrogen atmosphere Substances 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• 238000005160 1H NMR spectroscopy Methods 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
• 239000006185 dispersion Substances 0.000 description 12
• 239000000284 extract Substances 0.000 description 12
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 11
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 239000000908 ammonium hydroxide Substances 0.000 description 10
• 229910052938 sodium sulfate Inorganic materials 0.000 description 10
• 235000011152 sodium sulphate Nutrition 0.000 description 10
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 102100040247 Tumor necrosis factor Human genes 0.000 description 9
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
• ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• 230000028993 immune response Effects 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• 238000011282 treatment Methods 0.000 description 8
• SKPRPEJLFKCOAB-UHFFFAOYSA-N 3-nitroquinolin-4-amine Chemical compound C1=CC=C2C(N)=C([N+]([O-])=O)C=NC2=C1 SKPRPEJLFKCOAB-UHFFFAOYSA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• 206010028980 Neoplasm Diseases 0.000 description 7
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• 230000006698 induction Effects 0.000 description 7
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 239000003039 volatile agent Substances 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• 150000001204 N-oxides Chemical class 0.000 description 6
• 235000019502 Orange oil Nutrition 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• 239000012230 colorless oil Substances 0.000 description 6
• 239000012065 filter cake Substances 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• 239000010502 orange oil Substances 0.000 description 6
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• UTOMICFLROGMAE-UHFFFAOYSA-N quinoline-3,4-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CN=C21 UTOMICFLROGMAE-UHFFFAOYSA-N 0.000 description 6
• 238000001953 recrystallisation Methods 0.000 description 6
• 230000009467 reduction Effects 0.000 description 6
• 239000002002 slurry Substances 0.000 description 6
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 6
• OYWWLSSJJDHFCX-UHFFFAOYSA-N 4-n-[2-(2-methylsulfonylethoxy)ethyl]quinoline-3,4-diamine Chemical compound C1=CC=C2C(NCCOCCS(=O)(=O)C)=C(N)C=NC2=C1 OYWWLSSJJDHFCX-UHFFFAOYSA-N 0.000 description 5
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
• 239000002480 mineral oil Substances 0.000 description 5
• 235000010446 mineral oil Nutrition 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 238000010189 synthetic method Methods 0.000 description 5
• XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical compound C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 4
• 101150043532 CISH gene Proteins 0.000 description 4
• 238000002965 ELISA Methods 0.000 description 4
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
• 102000014150 Interferons Human genes 0.000 description 4
• 108010050904 Interferons Proteins 0.000 description 4
• 208000036142 Viral infection Diseases 0.000 description 4
• YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 4
• 239000012455 biphasic mixture Substances 0.000 description 4
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 239000013058 crude material Substances 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 229940079322 interferon Drugs 0.000 description 4
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
• 235000019341 magnesium sulphate Nutrition 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• 239000003607 modifier Substances 0.000 description 4
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
• 230000003647 oxidation Effects 0.000 description 4
• 238000007254 oxidation reaction Methods 0.000 description 4
• NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 4
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• 125000003396 thiol group Chemical class [H]S* 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 230000009385 viral infection Effects 0.000 description 4
• 238000010626 work up procedure Methods 0.000 description 4
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
• RHLMKKLAHKOLDK-UHFFFAOYSA-N 1-[2-(3-chloropropoxy)ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCOCCCCl)C3=C(N)N=C21 RHLMKKLAHKOLDK-UHFFFAOYSA-N 0.000 description 3
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