JP2007513170A - スルホン置換イミダゾ環エーテル - Google Patents
スルホン置換イミダゾ環エーテル Download PDFInfo
- Publication number
- JP2007513170A JP2007513170A JP2006542750A JP2006542750A JP2007513170A JP 2007513170 A JP2007513170 A JP 2007513170A JP 2006542750 A JP2006542750 A JP 2006542750A JP 2006542750 A JP2006542750 A JP 2006542750A JP 2007513170 A JP2007513170 A JP 2007513170A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- heterocyclyl
- alkylenyl
- heteroaryl
- Prior art date
- 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.)
- Pending
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 31
- 125000001174 sulfone group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 148
- -1 sulfinyl- Chemical group 0.000 claims abstract description 125
- 238000000034 method Methods 0.000 claims abstract description 50
- 102000004127 Cytokines Human genes 0.000 claims abstract description 26
- 108090000695 Cytokines Proteins 0.000 claims abstract description 26
- 241001465754 Metazoa Species 0.000 claims abstract description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
- 230000003612 virological effect Effects 0.000 claims abstract description 13
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 454
- 125000005466 alkylenyl group Chemical group 0.000 claims description 280
- 125000000623 heterocyclic group Chemical group 0.000 claims description 261
- 125000001072 heteroaryl group Chemical group 0.000 claims description 229
- 125000003118 aryl group Chemical group 0.000 claims description 182
- 125000003342 alkenyl group Chemical group 0.000 claims description 159
- 125000000304 alkynyl group Chemical group 0.000 claims description 155
- 125000002947 alkylene group Chemical group 0.000 claims description 137
- 125000003545 alkoxy group Chemical group 0.000 claims description 125
- 229910052739 hydrogen Inorganic materials 0.000 claims description 118
- 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 114
- 150000003839 salts Chemical class 0.000 claims description 114
- 125000004104 aryloxy group Chemical group 0.000 claims description 99
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 99
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 85
- 229910052799 carbon Inorganic materials 0.000 claims description 71
- 125000001424 substituent group Chemical group 0.000 claims description 70
- 229910052736 halogen Inorganic materials 0.000 claims description 63
- 150000002367 halogens Chemical class 0.000 claims description 62
- 150000002431 hydrogen Chemical class 0.000 claims description 61
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 125000003282 alkyl amino group Chemical group 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
- 125000000732 arylene group Chemical group 0.000 claims description 49
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 48
- 125000005549 heteroarylene group Chemical group 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 46
- 125000005842 heteroatom Chemical group 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000001188 haloalkyl group Chemical group 0.000 claims description 36
- 229920006395 saturated elastomer Polymers 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 23
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 23
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 23
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 230000002452 interceptive effect Effects 0.000 claims description 14
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 13
- 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
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 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
- 125000001313 C5-C10 heteroaryl group Chemical group 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
- 239000003937 drug carrier Substances 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 11
- 230000001419 dependent effect Effects 0.000 claims 4
- 239000000543 intermediate Substances 0.000 abstract description 7
- 230000006698 induction Effects 0.000 abstract description 6
- 239000002955 immunomodulating agent Substances 0.000 abstract description 3
- 229940121354 immunomodulator Drugs 0.000 abstract description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 125000000101 thioether group Chemical group 0.000 abstract description 2
- VFTLXHXYGQSOEN-UHFFFAOYSA-N 1h-imidazo[4,5-b][1,8]naphthyridine Chemical compound C1=CN=C2NC3=NC=NC3=CC2=C1 VFTLXHXYGQSOEN-UHFFFAOYSA-N 0.000 abstract 1
- JDQVYSWJFCKKPX-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-h]quinoline Chemical compound C1CCNC2=C1C=CC1=C2N=CN1 JDQVYSWJFCKKPX-UHFFFAOYSA-N 0.000 abstract 1
- BFRANVFNZVZMBU-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-imidazo[4,5-b][1,8]naphthyridine Chemical compound C1C2=NC=NC2=NC2=C1CCCN2 BFRANVFNZVZMBU-UHFFFAOYSA-N 0.000 abstract 1
- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 229940124669 imidazoquinoline Drugs 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 356
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 201
- 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 129
- 238000006243 chemical reaction Methods 0.000 description 119
- 239000011541 reaction mixture Substances 0.000 description 105
- 239000007787 solid Substances 0.000 description 105
- 239000000243 solution Substances 0.000 description 103
- 239000000463 material Substances 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
- 239000003921 oil Substances 0.000 description 72
- 235000019198 oils Nutrition 0.000 description 72
- 239000000203 mixture Substances 0.000 description 71
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
- 238000004458 analytical method Methods 0.000 description 67
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- 239000000741 silica gel Substances 0.000 description 50
- 229910002027 silica gel Inorganic materials 0.000 description 50
- 238000001914 filtration Methods 0.000 description 47
- 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 40
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 38
- 239000007858 starting material Substances 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- 150000001721 carbon Chemical group 0.000 description 34
- 239000012043 crude product Substances 0.000 description 32
- 239000000843 powder Substances 0.000 description 31
- 239000013078 crystal Substances 0.000 description 29
- 239000012044 organic layer Substances 0.000 description 29
- 238000010992 reflux Methods 0.000 description 28
- 238000004440 column chromatography Methods 0.000 description 26
- 238000007796 conventional method Methods 0.000 description 26
- 239000006260 foam 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
- 238000003756 stirring Methods 0.000 description 25
- 238000004809 thin layer chromatography Methods 0.000 description 23
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 22
- 239000012312 sodium hydride Substances 0.000 description 22
- 229910000104 sodium hydride Inorganic materials 0.000 description 22
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 20
- 238000003818 flash chromatography Methods 0.000 description 20
- 229910000029 sodium carbonate Inorganic materials 0.000 description 19
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- 238000000746 purification Methods 0.000 description 16
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- WUIJTQZXUURFQU-UHFFFAOYSA-N 1-methylsulfonylethene Chemical compound CS(=O)(=O)C=C WUIJTQZXUURFQU-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 239000000284 extract Substances 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 description 12
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical class C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 235000011114 ammonium hydroxide Nutrition 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 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 11
- 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 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 125000003396 thiol group Chemical class [H]S* 0.000 description 11
- 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
- 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 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 230000028993 immune response Effects 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 7
- 239000003039 volatile agent Substances 0.000 description 7
- 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 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
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 6
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 6
- 241000700605 Viruses Species 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 239000010502 orange oil Substances 0.000 description 6
- 239000012071 phase Substances 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
- 239000002002 slurry Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 102000006992 Interferon-alpha Human genes 0.000 description 5
- 108010047761 Interferon-alpha Proteins 0.000 description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- JYYSVVKAKJIJBG-UHFFFAOYSA-N 2-(methoxymethyl)-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(COC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 JYYSVVKAKJIJBG-UHFFFAOYSA-N 0.000 description 4
- LKPSHWDWAACDSB-UHFFFAOYSA-N 2-butyl-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CCCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 LKPSHWDWAACDSB-UHFFFAOYSA-N 0.000 description 4
- QPYPPXSGTYPRNK-UHFFFAOYSA-N 2-ethyl-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 QPYPPXSGTYPRNK-UHFFFAOYSA-N 0.000 description 4
- YHQPYMQQMBVULM-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C1N=C(N)C1=C2NC=N1 YHQPYMQQMBVULM-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 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
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 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
- OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 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
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000006722 reduction reaction Methods 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
- XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- KXWRFYFLFIFPLL-UHFFFAOYSA-N 1-[2-(2-methylsulfonylethoxy)ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CCC)=N3)CCOCCS(C)(=O)=O)C3=C(N)N=C21 KXWRFYFLFIFPLL-UHFFFAOYSA-N 0.000 description 3
- NTTWTHPSHHVJFX-UHFFFAOYSA-N 1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 NTTWTHPSHHVJFX-UHFFFAOYSA-N 0.000 description 3
- ZRSFXZQDZXJXQU-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclobutyl]methyl]imidazo[4,5-c]quinolin-4-amine Chemical group CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CCC1 ZRSFXZQDZXJXQU-UHFFFAOYSA-N 0.000 description 3
- QFQIGDPCSVPGAG-UHFFFAOYSA-N 2-[2-(2-methylsulfonylethoxy)ethyl]quinoline-3,4-diamine Chemical compound C1=CC=C2C(N)=C(N)C(CCOCCS(=O)(=O)C)=NC2=C1 QFQIGDPCSVPGAG-UHFFFAOYSA-N 0.000 description 3
- RLBLAOGOGZWKCE-UHFFFAOYSA-N 2-methyl-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(C)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 RLBLAOGOGZWKCE-UHFFFAOYSA-N 0.000 description 3
- KAHKXUXOXXKPLO-UHFFFAOYSA-N 3-aminooxypropan-1-ol Chemical compound NOCCCO KAHKXUXOXXKPLO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 238000005576 amination reaction Methods 0.000 description 3
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 2
- JAFMOTJMRSZOJE-UHFFFAOYSA-N 1,1,1-trimethoxybutane Chemical compound CCCC(OC)(OC)OC JAFMOTJMRSZOJE-UHFFFAOYSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- VHESTMWKMZSBIP-UHFFFAOYSA-N 1-(3,4-diamino-3H-1,5-naphthyridin-4-yl)-2-methylpropan-2-ol Chemical compound OC(CC1(C(C=NC2=CC=CN=C12)N)N)(C)C VHESTMWKMZSBIP-UHFFFAOYSA-N 0.000 description 2
- QMRGVILFWQUZKR-UHFFFAOYSA-N 1-(aminomethyl)cyclobutan-1-ol Chemical compound NCC1(O)CCC1 QMRGVILFWQUZKR-UHFFFAOYSA-N 0.000 description 2
- FEALJKFIUQDJAV-UHFFFAOYSA-N 1-(aminomethyl)cyclopentan-1-ol Chemical compound NCC1(O)CCCC1 FEALJKFIUQDJAV-UHFFFAOYSA-N 0.000 description 2
- UFRDYBOWVGFYJB-UHFFFAOYSA-N 1-(nitromethyl)cyclobutan-1-ol Chemical compound [O-][N+](=O)CC1(O)CCC1 UFRDYBOWVGFYJB-UHFFFAOYSA-N 0.000 description 2
- BORHRVRLEZGVIM-UHFFFAOYSA-N 1-(nitromethyl)cyclopentan-1-ol Chemical compound [O-][N+](=O)CC1(O)CCCC1 BORHRVRLEZGVIM-UHFFFAOYSA-N 0.000 description 2
- NSCQJWRTRFMDDX-UHFFFAOYSA-N 1-[2-(2-methylsulfonylethoxy)ethyl]-2-propyl-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(CCC)=N3)CCOCCS(C)(=O)=O)C3=C(N)N=C21 NSCQJWRTRFMDDX-UHFFFAOYSA-N 0.000 description 2
- KUYODFWUNZNBGJ-UHFFFAOYSA-N 1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C3N(CCOCCS(=O)(=O)C)C=NC3=C(N)N=C21 KUYODFWUNZNBGJ-UHFFFAOYSA-N 0.000 description 2
- FYLFIYBEHMYIQB-UHFFFAOYSA-N 1-[2-(3-chloropropoxy)ethyl]-2-propylimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCOCCCCl)C3=CN=C21 FYLFIYBEHMYIQB-UHFFFAOYSA-N 0.000 description 2
- ITRWTSFAXIVQLI-UHFFFAOYSA-N 1-[2-(3-decylsulfonylpropoxy)ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C3N(CCOCCCS(=O)(=O)CCCCCCCCCC)C(CCC)=NC3=C(N)N=C21 ITRWTSFAXIVQLI-UHFFFAOYSA-N 0.000 description 2
- CTWXFCJKLDDPIM-UHFFFAOYSA-N 1-[2-(3-propan-2-ylsulfonylpropoxy)ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CCC)=N3)CCOCCCS(=O)(=O)C(C)C)C3=C(N)N=C21 CTWXFCJKLDDPIM-UHFFFAOYSA-N 0.000 description 2
- YHPROTUOYWKNIM-UHFFFAOYSA-N 1-[2-(ethoxymethyl)imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol Chemical compound C1=CC=NC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=CN=C21 YHPROTUOYWKNIM-UHFFFAOYSA-N 0.000 description 2
- MYKUTOOCWPZANP-UHFFFAOYSA-N 1-[2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=CN=C21 MYKUTOOCWPZANP-UHFFFAOYSA-N 0.000 description 2
- LJXJFLYHGXTWOT-UHFFFAOYSA-N 1-[2-[3-(2-methylphenyl)sulfonylpropoxy]ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical group CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCOCCCS(=O)(=O)C1=CC=CC=C1C LJXJFLYHGXTWOT-UHFFFAOYSA-N 0.000 description 2
- HAGCINMJOPAJFX-UHFFFAOYSA-N 1-[2-[3-(benzenesulfonyl)propoxy]ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical group CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCOCCCS(=O)(=O)C1=CC=CC=C1 HAGCINMJOPAJFX-UHFFFAOYSA-N 0.000 description 2
- INFAEAGGRRVJMW-UHFFFAOYSA-N 1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-2-propyl-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(CCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 INFAEAGGRRVJMW-UHFFFAOYSA-N 0.000 description 2
- JBUUIXDZARHLOA-UHFFFAOYSA-N 1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C3N(CC(C)(C)OCCS(C)(=O)=O)C=NC3=C(N)N=C21 JBUUIXDZARHLOA-UHFFFAOYSA-N 0.000 description 2
- YCIZLUVXERWPDG-UHFFFAOYSA-N 1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C3N(CC(C)(C)OCCS(C)(=O)=O)C=NC3=C(N)N=C21 YCIZLUVXERWPDG-UHFFFAOYSA-N 0.000 description 2
- FVHQMODUIGOFJT-UHFFFAOYSA-N 1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol Chemical compound C1=CC=NC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=C(N)N=C21 FVHQMODUIGOFJT-UHFFFAOYSA-N 0.000 description 2
- QMPDPPZINVLMPH-UHFFFAOYSA-N 1-[[(3-aminoquinolin-4-yl)amino]methyl]cyclobutan-1-ol Chemical compound NC1=CN=C2C=CC=CC2=C1NCC1(O)CCC1 QMPDPPZINVLMPH-UHFFFAOYSA-N 0.000 description 2
- ABAYXPDXUHPOJV-UHFFFAOYSA-N 1-[[(3-aminoquinolin-4-yl)amino]methyl]cyclopentan-1-ol Chemical compound NC1=CN=C2C=CC=CC2=C1NCC1(O)CCCC1 ABAYXPDXUHPOJV-UHFFFAOYSA-N 0.000 description 2
- ZWVSAAKVTUGQFR-UHFFFAOYSA-N 1-[[(3-nitroquinolin-4-yl)amino]methyl]cyclobutan-1-ol Chemical compound [O-][N+](=O)C=1C=NC2=CC=CC=C2C=1NCC1(O)CCC1 ZWVSAAKVTUGQFR-UHFFFAOYSA-N 0.000 description 2
- XDXRYOOTWLBTPN-UHFFFAOYSA-N 1-[[(3-nitroquinolin-4-yl)amino]methyl]cyclohexan-1-ol Chemical compound [O-][N+](=O)C=1C=NC2=CC=CC=C2C=1NCC1(O)CCCCC1 XDXRYOOTWLBTPN-UHFFFAOYSA-N 0.000 description 2
- AJPFPTNCVOTWRH-UHFFFAOYSA-N 1-[[(3-nitroquinolin-4-yl)amino]methyl]cyclopentan-1-ol Chemical compound [O-][N+](=O)C=1C=NC2=CC=CC=C2C=1NCC1(O)CCCC1 AJPFPTNCVOTWRH-UHFFFAOYSA-N 0.000 description 2
- DBHCAXWZZFNYRC-UHFFFAOYSA-N 1-[[(3-nitroquinolin-4-yl)amino]methyl]cyclopropan-1-ol Chemical compound [O-][N+](=O)C=1C=NC2=CC=CC=C2C=1NCC1(O)CC1 DBHCAXWZZFNYRC-UHFFFAOYSA-N 0.000 description 2
- WOKLIKJAHVTAEW-UHFFFAOYSA-N 1-[[2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]methyl]cyclohexan-1-ol Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC1(O)CCCCC1 WOKLIKJAHVTAEW-UHFFFAOYSA-N 0.000 description 2
- JUZJOOIAICCOKY-UHFFFAOYSA-N 1-[[2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]methyl]cyclopropan-1-ol Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC1(O)CC1 JUZJOOIAICCOKY-UHFFFAOYSA-N 0.000 description 2
- HKLGLOVZQOLJPP-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CCOC)=N3)CCOCCS(C)(=O)=O)C3=C(N)N=C21 HKLGLOVZQOLJPP-UHFFFAOYSA-N 0.000 description 2
- FJKBNCRNYQIRQI-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(COCC)=N3)CCOCCS(C)(=O)=O)C3=C(N)N=C21 FJKBNCRNYQIRQI-UHFFFAOYSA-N 0.000 description 2
- IQAWTJJTDNURTR-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(COCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 IQAWTJJTDNURTR-UHFFFAOYSA-N 0.000 description 2
- DOAMQILLXIGMSJ-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical group C1=CC=NC2=C(N(C(COCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 DOAMQILLXIGMSJ-UHFFFAOYSA-N 0.000 description 2
- XSDUPKYNJMKXGF-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclobutyl]methyl]-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C3CCCCC3=C2N1CC1(OCCS(C)(=O)=O)CCC1 XSDUPKYNJMKXGF-UHFFFAOYSA-N 0.000 description 2
- NJDCMYUORORQPL-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclohexyl]methyl]imidazo[4,5-c]quinolin-4-amine Chemical group CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CCCCC1 NJDCMYUORORQPL-UHFFFAOYSA-N 0.000 description 2
- IRJJQOJXABHFIJ-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclopentyl]methyl]imidazo[4,5-c]quinolin-4-amine Chemical group CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CCCC1 IRJJQOJXABHFIJ-UHFFFAOYSA-N 0.000 description 2
- HYYVUPRCPRQNDW-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclopropyl]methyl]imidazo[4,5-c]quinolin-4-amine Chemical group CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CC1 HYYVUPRCPRQNDW-UHFFFAOYSA-N 0.000 description 2
- CCUBHXUAUMGEBT-UHFFFAOYSA-N 2-(methoxymethyl)-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(COC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 CCUBHXUAUMGEBT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 2
- VSRNHWSMRQEFAL-UHFFFAOYSA-N 2-hexyl-1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CCCCCC)=N3)CCOCCS(C)(=O)=O)C3=C(N)N=C21 VSRNHWSMRQEFAL-UHFFFAOYSA-N 0.000 description 2
- AWJHHYFVBBAYKE-UHFFFAOYSA-N 2-methyl-1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(C)=N3)CCOCCS(C)(=O)=O)C3=C(N)N=C21 AWJHHYFVBBAYKE-UHFFFAOYSA-N 0.000 description 2
- WDAOOTVRGLOILV-UHFFFAOYSA-N 2-methyl-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(C)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 WDAOOTVRGLOILV-UHFFFAOYSA-N 0.000 description 2
- IJCAVJRFSFDTMC-UHFFFAOYSA-N 2-propyl-1-[2-(3-pyridin-2-ylsulfonylpropoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical group CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCOCCCS(=O)(=O)C1=CC=CC=N1 IJCAVJRFSFDTMC-UHFFFAOYSA-N 0.000 description 2
- GALJZRVFTQQJLR-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,7]naphthyridine Chemical compound C1=NC=CC2=C(NC=N3)C3=CN=C21 GALJZRVFTQQJLR-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 241000606161 Chlamydia Species 0.000 description 2
- 208000001490 Dengue Diseases 0.000 description 2
- 206010012310 Dengue fever Diseases 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- 241000709661 Enterovirus Species 0.000 description 2
- 208000010201 Exanthema Diseases 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 108010002352 Interleukin-1 Proteins 0.000 description 2
- 102000000589 Interleukin-1 Human genes 0.000 description 2
- 102000003814 Interleukin-10 Human genes 0.000 description 2
- 108090000174 Interleukin-10 Proteins 0.000 description 2
- 102000013462 Interleukin-12 Human genes 0.000 description 2
- 108010065805 Interleukin-12 Proteins 0.000 description 2
- 108090001005 Interleukin-6 Proteins 0.000 description 2
- 102000004889 Interleukin-6 Human genes 0.000 description 2
- 102000015696 Interleukins Human genes 0.000 description 2
- 108010063738 Interleukins Proteins 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 241001631646 Papillomaviridae Species 0.000 description 2
- 206010035148 Plague Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000003152 Yellow Fever Diseases 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 210000003719 b-lymphocyte Anatomy 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000000601 blood cell Anatomy 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 208000025729 dengue disease Diseases 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 201000005884 exanthem Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 208000006454 hepatitis Diseases 0.000 description 2
- 231100000283 hepatitis Toxicity 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- MLHUGDNMASYREH-UHFFFAOYSA-N n-[2-(2-methylsulfonylethoxy)ethyl]-3-nitroquinolin-4-amine Chemical compound C1=CC=C2C(NCCOCCS(=O)(=O)C)=C([N+]([O-])=O)C=NC2=C1 MLHUGDNMASYREH-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 2
- 206010037844 rash Diseases 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 201000010153 skin papilloma Diseases 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 2
- NQHKCHWQDDWQJR-UHFFFAOYSA-M sodium;propane-2-thiolate Chemical compound [Na+].CC(C)[S-] NQHKCHWQDDWQJR-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- 241000701161 unidentified adenovirus Species 0.000 description 2
- 239000012646 vaccine adjuvant Substances 0.000 description 2
- 229940124931 vaccine adjuvant Drugs 0.000 description 2
- 230000029663 wound healing Effects 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LSRVEPKOAZIZPE-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridin-4-amine Chemical class C1=CC=C2C(N)CCNC2=N1 LSRVEPKOAZIZPE-UHFFFAOYSA-N 0.000 description 1
- ZCZVGQCBSJLDDS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine Chemical compound C1=CC=C2CCCNC2=N1 ZCZVGQCBSJLDDS-UHFFFAOYSA-N 0.000 description 1
- UZAOPTDGCXICDB-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-4-amine Chemical class C1=CC=C2C(N)CCNC2=C1 UZAOPTDGCXICDB-UHFFFAOYSA-N 0.000 description 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- YAFRGSCKSGCBIS-UHFFFAOYSA-N 1-(2-butylimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CC(C)(C)O)C3=CN=C21 YAFRGSCKSGCBIS-UHFFFAOYSA-N 0.000 description 1
- YJKZDGOMTKOYQK-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1CCC1CCNCC1 YJKZDGOMTKOYQK-UHFFFAOYSA-N 0.000 description 1
- HDDNSPWJCZZICL-UHFFFAOYSA-N 1-(6-methoxyquinolin-8-yl)-2-methylimidazo[4,5-c]quinoline Chemical compound N1=CC=CC2=CC(OC)=CC(N3C4=C5C=CC=CC5=NC=C4N=C3C)=C21 HDDNSPWJCZZICL-UHFFFAOYSA-N 0.000 description 1
- DXIAEURKHWGAFH-UHFFFAOYSA-N 1-(aminomethyl)cyclohexan-1-ol;hydron;chloride Chemical compound Cl.NCC1(O)CCCCC1 DXIAEURKHWGAFH-UHFFFAOYSA-N 0.000 description 1
- JXJORHGRCCODBV-UHFFFAOYSA-N 1-(aminomethyl)cyclopropan-1-ol Chemical compound NCC1(O)CC1 JXJORHGRCCODBV-UHFFFAOYSA-N 0.000 description 1
- LHBODUUXCWHZLN-UHFFFAOYSA-N 1-[(3-aminoquinolin-4-yl)amino]-2-methylpropan-2-ol Chemical compound C1=CC=C2C(NCC(C)(O)C)=C(N)C=NC2=C1 LHBODUUXCWHZLN-UHFFFAOYSA-N 0.000 description 1
- VYOOANQPEZIGNX-UHFFFAOYSA-N 1-[2-(2-methylsulfonylethoxy)ethyl]-2-propylimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCOCCS(C)(=O)=O)C3=CN=C21 VYOOANQPEZIGNX-UHFFFAOYSA-N 0.000 description 1
- IYSOUQYLGAUCFZ-UHFFFAOYSA-N 1-[2-(3-methylsulfinylpropoxy)ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCOCCCS(C)=O)C3=C(N)N=C21 IYSOUQYLGAUCFZ-UHFFFAOYSA-N 0.000 description 1
- YTOIDNHMOAYCFO-UHFFFAOYSA-N 1-[2-(3-methylsulfonylpropoxy)ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCOCCCS(C)(=O)=O)C3=C(N)N=C21 YTOIDNHMOAYCFO-UHFFFAOYSA-N 0.000 description 1
- SCWRILWSTQJVPC-UHFFFAOYSA-N 1-[2-(3-phenylsulfanylpropoxy)ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCOCCCSC1=CC=CC=C1 SCWRILWSTQJVPC-UHFFFAOYSA-N 0.000 description 1
- WCKGKRSEIHJDND-UHFFFAOYSA-N 1-[2-(3-propan-2-ylsulfanylpropoxy)ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCOCCCSC(C)C)C3=C(N)N=C21 WCKGKRSEIHJDND-UHFFFAOYSA-N 0.000 description 1
- VFACSZBWLCKZTH-UHFFFAOYSA-N 1-[2-(methoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol Chemical compound C1=CC=CC2=C(N(C(COC)=N3)CC(C)(C)O)C3=CN=C21 VFACSZBWLCKZTH-UHFFFAOYSA-N 0.000 description 1
- JPZFRTCRHRIQTD-UHFFFAOYSA-N 1-[2-[2-(benzenesulfonyl)ethoxy]-2-methylpropyl]-2-(ethoxymethyl)-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound CCOCC1=NC2=C[N+]([O-])=C3C=CC=CC3=C2N1CC(C)(C)OCCS(=O)(=O)C1=CC=CC=C1 JPZFRTCRHRIQTD-UHFFFAOYSA-N 0.000 description 1
- GCTDVMLCEZSPFM-UHFFFAOYSA-N 1-[2-[2-(benzenesulfonyl)ethoxy]-2-methylpropyl]-2-(ethoxymethyl)imidazo[4,5-c]quinolin-4-amine Chemical group CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)(C)OCCS(=O)(=O)C1=CC=CC=C1 GCTDVMLCEZSPFM-UHFFFAOYSA-N 0.000 description 1
- UVDQWNAEIOCOAO-UHFFFAOYSA-N 1-[2-[2-(benzenesulfonyl)ethoxy]-2-methylpropyl]-2-(ethoxymethyl)imidazo[4,5-c]quinoline Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC(C)(C)OCCS(=O)(=O)C1=CC=CC=C1 UVDQWNAEIOCOAO-UHFFFAOYSA-N 0.000 description 1
- FOENADIBQOENBL-UHFFFAOYSA-N 1-[2-[3-(2-methylphenyl)sulfanylpropoxy]ethyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCOCCCSC1=CC=CC=C1C FOENADIBQOENBL-UHFFFAOYSA-N 0.000 description 1
- YQLFEORHTDFUQC-UHFFFAOYSA-N 1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-2-propylimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=CN=C21 YQLFEORHTDFUQC-UHFFFAOYSA-N 0.000 description 1
- KWMAERBKDOCSSN-UHFFFAOYSA-N 1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-5-oxido-2-propylimidazo[4,5-c]quinolin-5-ium Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C[N+]([O-])=C21 KWMAERBKDOCSSN-UHFFFAOYSA-N 0.000 description 1
- ACWCVMQOGWDIAS-UHFFFAOYSA-N 1-[[2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]methyl]cyclobutan-1-ol Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC1(O)CCC1 ACWCVMQOGWDIAS-UHFFFAOYSA-N 0.000 description 1
- OFCKYYPCUPWJMB-UHFFFAOYSA-N 1-[[2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]methyl]cyclopentan-1-ol Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC1(O)CCCC1 OFCKYYPCUPWJMB-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- UHUHBFMZVCOEOV-UHFFFAOYSA-N 1h-imidazo[4,5-c]pyridin-4-amine Chemical class NC1=NC=CC2=C1N=CN2 UHUHBFMZVCOEOV-UHFFFAOYSA-N 0.000 description 1
- XSAUTYJOZCCENE-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCOCCS(C)(=O)=O)C3=CN=C21 XSAUTYJOZCCENE-UHFFFAOYSA-N 0.000 description 1
- MJNZJJLGCIWTEP-UHFFFAOYSA-N 2-(2-methylsulfonylethoxy)ethanamine;hydrochloride Chemical compound Cl.CS(=O)(=O)CCOCCN MJNZJJLGCIWTEP-UHFFFAOYSA-N 0.000 description 1
- CSVAJAZOXVYLMC-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 CSVAJAZOXVYLMC-UHFFFAOYSA-N 0.000 description 1
- LOHMWGKYBPYRPQ-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=CN=C21 LOHMWGKYBPYRPQ-UHFFFAOYSA-N 0.000 description 1
- QKXGMDDWGOWKDQ-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclobutyl]methyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound CCOCC1=NC2=C[N+]([O-])=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CCC1 QKXGMDDWGOWKDQ-UHFFFAOYSA-N 0.000 description 1
- QIXKUBFLCUZGCX-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclobutyl]methyl]imidazo[4,5-c]quinoline Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CCC1 QIXKUBFLCUZGCX-UHFFFAOYSA-N 0.000 description 1
- YMSFGRPYBUEROS-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclohexyl]methyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound CCOCC1=NC2=C[N+]([O-])=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CCCCC1 YMSFGRPYBUEROS-UHFFFAOYSA-N 0.000 description 1
- CWQNGBMLGZDWJC-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclohexyl]methyl]imidazo[4,5-c]quinoline Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CCCCC1 CWQNGBMLGZDWJC-UHFFFAOYSA-N 0.000 description 1
- ZMVSFBUOKQGHFT-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclopentyl]methyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound CCOCC1=NC2=C[N+]([O-])=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CCCC1 ZMVSFBUOKQGHFT-UHFFFAOYSA-N 0.000 description 1
- GAHYAVQXKIFIGF-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclopentyl]methyl]imidazo[4,5-c]quinoline Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CCCC1 GAHYAVQXKIFIGF-UHFFFAOYSA-N 0.000 description 1
- WOEXTTGJJHITNJ-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[[1-(2-methylsulfonylethoxy)cyclopropyl]methyl]imidazo[4,5-c]quinoline Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC1(OCCS(C)(=O)=O)CC1 WOEXTTGJJHITNJ-UHFFFAOYSA-N 0.000 description 1
- WNRPMTBLWBTGRQ-UHFFFAOYSA-N 2-(methoxymethyl)-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound C1=CC=CC2=C(N(C(COC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C[N+]([O-])=C21 WNRPMTBLWBTGRQ-UHFFFAOYSA-N 0.000 description 1
- DSOAEACVFMBYAT-UHFFFAOYSA-N 2-(methoxymethyl)-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(COC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=CN=C21 DSOAEACVFMBYAT-UHFFFAOYSA-N 0.000 description 1
- MWLRZEOXRJPWHU-UHFFFAOYSA-N 2-butyl-1-[2-(2-methylsulfonylethoxy)ethyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCOCCS(C)(=O)=O)C3=C[N+]([O-])=C21 MWLRZEOXRJPWHU-UHFFFAOYSA-N 0.000 description 1
- AOIHSZVQPODGGY-UHFFFAOYSA-N 2-butyl-1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CCCC)=N3)CCOCCS(C)(=O)=O)C3=C(N)N=C21 AOIHSZVQPODGGY-UHFFFAOYSA-N 0.000 description 1
- AKGCTVWAAQPEPW-UHFFFAOYSA-N 2-butyl-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C[N+]([O-])=C21 AKGCTVWAAQPEPW-UHFFFAOYSA-N 0.000 description 1
- YWDGOMOQAZENKS-UHFFFAOYSA-N 2-butyl-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(CCCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 YWDGOMOQAZENKS-UHFFFAOYSA-N 0.000 description 1
- RUPZWAUQVJYUKA-UHFFFAOYSA-N 2-butyl-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=CN=C21 RUPZWAUQVJYUKA-UHFFFAOYSA-N 0.000 description 1
- PQZXGIIGQHCVAU-UHFFFAOYSA-N 2-chloro-3-nitroquinoline Chemical compound C1=CC=C2N=C(Cl)C([N+](=O)[O-])=CC2=C1 PQZXGIIGQHCVAU-UHFFFAOYSA-N 0.000 description 1
- LKJCTOWKRYYFLG-UHFFFAOYSA-N 2-ethyl-1-[2-(2-methylsulfonylethoxy)ethyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCOCCS(C)(=O)=O)C3=C[N+]([O-])=C21 LKJCTOWKRYYFLG-UHFFFAOYSA-N 0.000 description 1
- XDNVMWQAIBTBGM-UHFFFAOYSA-N 2-ethyl-1-[2-(2-methylsulfonylethoxy)ethyl]-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(CC)=N3)CCOCCS(C)(=O)=O)C3=C(N)N=C21 XDNVMWQAIBTBGM-UHFFFAOYSA-N 0.000 description 1
- LOJHYNOAHCIOAT-UHFFFAOYSA-N 2-ethyl-1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CC)=N3)CCOCCS(C)(=O)=O)C3=C(N)N=C21 LOJHYNOAHCIOAT-UHFFFAOYSA-N 0.000 description 1
- SSAXMPONQYXDAJ-UHFFFAOYSA-N 2-ethyl-1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCOCCS(C)(=O)=O)C3=CN=C21 SSAXMPONQYXDAJ-UHFFFAOYSA-N 0.000 description 1
- URGSRAWYGLXSJC-UHFFFAOYSA-N 2-ethyl-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(CC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(N)N=C21 URGSRAWYGLXSJC-UHFFFAOYSA-N 0.000 description 1
- VJLAOMJADGGWCA-UHFFFAOYSA-N 2-ethyl-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=CN=C21 VJLAOMJADGGWCA-UHFFFAOYSA-N 0.000 description 1
- VXIWFLBECQKZSE-UHFFFAOYSA-N 2-hexyl-1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCCCCC)=N3)CCOCCS(C)(=O)=O)C3=CN=C21 VXIWFLBECQKZSE-UHFFFAOYSA-N 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- JOPIWQHCFMTREO-UHFFFAOYSA-N 2-methyl-1-(2-propylimidazo[4,5-c]quinolin-1-yl)propan-2-ol Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CC(C)(C)O)C3=CN=C21 JOPIWQHCFMTREO-UHFFFAOYSA-N 0.000 description 1
- HMBBEVMGBHTFAV-UHFFFAOYSA-N 2-methyl-1-[(3-nitro-1,5-naphthyridin-4-yl)amino]propan-2-ol Chemical compound C1=CN=C2C(NCC(C)(O)C)=C([N+]([O-])=O)C=NC2=C1 HMBBEVMGBHTFAV-UHFFFAOYSA-N 0.000 description 1
- UUIJTARFZIWNCK-UHFFFAOYSA-N 2-methyl-1-[(3-nitroquinolin-4-yl)amino]propan-2-ol Chemical compound C1=CC=C2C(NCC(C)(O)C)=C([N+]([O-])=O)C=NC2=C1 UUIJTARFZIWNCK-UHFFFAOYSA-N 0.000 description 1
- RXYMDPNXIMXLPT-UHFFFAOYSA-N 2-methyl-1-[2-(2-methylsulfonylethoxy)ethyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCOCCS(C)(=O)=O)C3=C[N+]([O-])=C21 RXYMDPNXIMXLPT-UHFFFAOYSA-N 0.000 description 1
- ZUYCMODTWIZGSX-UHFFFAOYSA-N 2-methyl-1-[2-(2-methylsulfonylethoxy)ethyl]-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(C)=N3)CCOCCS(C)(=O)=O)C3=C(N)N=C21 ZUYCMODTWIZGSX-UHFFFAOYSA-N 0.000 description 1
- ZAOKQPQFMJKXNA-UHFFFAOYSA-N 2-methyl-1-[2-(2-methylsulfonylethoxy)ethyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCOCCS(C)(=O)=O)C3=CN=C21 ZAOKQPQFMJKXNA-UHFFFAOYSA-N 0.000 description 1
- QXDFOBZDLZFFFZ-UHFFFAOYSA-N 2-propyl-1-[2-(3-pyridin-2-ylsulfanylpropoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCOCCCSC1=CC=CC=N1 QXDFOBZDLZFFFZ-UHFFFAOYSA-N 0.000 description 1
- QGZJWCPDBUKLTB-UHFFFAOYSA-N 3-(2-aminoethoxy)propan-1-ol;hydrochloride Chemical compound Cl.NCCOCCCO QGZJWCPDBUKLTB-UHFFFAOYSA-N 0.000 description 1
- FERWBXLFSBWTDE-UHFFFAOYSA-N 3-aminobutan-2-ol Chemical compound CC(N)C(C)O FERWBXLFSBWTDE-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- VNAVBWOZJHYVTQ-UHFFFAOYSA-N 4-chloro-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CC(C)(C)OCCS(C)(=O)=O)C=NC3=C(Cl)N=C21 VNAVBWOZJHYVTQ-UHFFFAOYSA-N 0.000 description 1
- DHGAHSOULAPUOJ-UHFFFAOYSA-N 4-chloro-2-methyl-1-[2-methyl-2-(2-methylsulfonylethoxy)propyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(C)=N3)CC(C)(C)OCCS(C)(=O)=O)C3=C(Cl)N=C21 DHGAHSOULAPUOJ-UHFFFAOYSA-N 0.000 description 1
- RCBCVEHJAYUJSJ-UHFFFAOYSA-N 4-nitrotetrazolo[1,5-a][1,8]naphthyridine Chemical compound [O-][N+](=O)C1=CC2=CC=CN=C2N2C1=NN=N2 RCBCVEHJAYUJSJ-UHFFFAOYSA-N 0.000 description 1
- PQMPXLLOISRPOQ-UHFFFAOYSA-N 5-chloro-4-nitrotetrazolo[1,5-a][1,7]naphthyridine Chemical compound [O-][N+](=O)C1=C(Cl)C2=CC=NC=C2N2C1=NN=N2 PQMPXLLOISRPOQ-UHFFFAOYSA-N 0.000 description 1
- ZMFJYKCVLOHIMY-UHFFFAOYSA-N 5-oxido-4H-imidazo[4,5-c]quinolin-5-ium Chemical compound N1=CN=C2C[N+](=C3C=CC=CC3=C21)[O-] ZMFJYKCVLOHIMY-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 206010059313 Anogenital warts Diseases 0.000 description 1
- 201000002909 Aspergillosis Diseases 0.000 description 1
- 208000036641 Aspergillus infections Diseases 0.000 description 1
- 208000012657 Atopic disease Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
- 208000003950 B-cell lymphoma Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- 241000588807 Bordetella Species 0.000 description 1
- 241000589562 Brucella Species 0.000 description 1
- LIDRJGJEIJHOAR-UHFFFAOYSA-N C1=NC=C2N(NN=N3)C3=C3N=CN=C3C2=C1 Chemical compound C1=NC=C2N(NN=N3)C3=C3N=CN=C3C2=C1 LIDRJGJEIJHOAR-UHFFFAOYSA-N 0.000 description 1
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 1
- 241000589876 Campylobacter Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 206010008263 Cervical dysplasia Diseases 0.000 description 1
- 201000006082 Chickenpox Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010008631 Cholera Diseases 0.000 description 1
- 241000588881 Chromobacterium Species 0.000 description 1
- 241000193403 Clostridium Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 208000000907 Condylomata Acuminata Diseases 0.000 description 1
- 241000711573 Coronaviridae Species 0.000 description 1
- 241000186216 Corynebacterium Species 0.000 description 1
- 208000006081 Cryptococcal meningitis Diseases 0.000 description 1
- 208000008953 Cryptosporidiosis Diseases 0.000 description 1
- 206010011502 Cryptosporidiosis infection Diseases 0.000 description 1
- 241000701022 Cytomegalovirus Species 0.000 description 1
- 108010041986 DNA Vaccines Proteins 0.000 description 1
- 229940021995 DNA vaccine Drugs 0.000 description 1
- 206010011985 Decubitus ulcer Diseases 0.000 description 1
- 208000006926 Discoid Lupus Erythematosus Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 206010014596 Encephalitis Japanese B Diseases 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 206010014950 Eosinophilia Diseases 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 208000032027 Essential Thrombocythemia Diseases 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- 208000004729 Feline Leukemia Diseases 0.000 description 1
- 241000710831 Flavivirus Species 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 241000606790 Haemophilus Species 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 241000589989 Helicobacter Species 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 201000002563 Histoplasmosis Diseases 0.000 description 1
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108090000176 Interleukin-13 Proteins 0.000 description 1
- 108090000978 Interleukin-4 Proteins 0.000 description 1
- 108010002616 Interleukin-5 Proteins 0.000 description 1
- 201000005807 Japanese encephalitis Diseases 0.000 description 1
- 241000710842 Japanese encephalitis virus Species 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- 208000002260 Keloid Diseases 0.000 description 1
- 208000001126 Keratosis Diseases 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 241000222722 Leishmania <genus> Species 0.000 description 1
- 241000713666 Lentivirus Species 0.000 description 1
- 241000186781 Listeria Species 0.000 description 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
- 201000005505 Measles Diseases 0.000 description 1
- 241000712079 Measles morbillivirus Species 0.000 description 1
- 206010027209 Meningitis cryptococcal Diseases 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 208000005647 Mumps Diseases 0.000 description 1
- 241000711386 Mumps virus Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000588653 Neisseria Species 0.000 description 1
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 208000001388 Opportunistic Infections Diseases 0.000 description 1
- 241000700629 Orthopoxvirus Species 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241000709664 Picornaviridae Species 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 208000005384 Pneumocystis Pneumonia Diseases 0.000 description 1
- 206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 description 1
- 208000004210 Pressure Ulcer Diseases 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000588768 Providencia Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 206010037742 Rabies Diseases 0.000 description 1
- 108010008281 Recombinant Fusion Proteins Proteins 0.000 description 1
- 102000007056 Recombinant Fusion Proteins Human genes 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 241000702670 Rotavirus Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 208000001203 Smallpox Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 230000024932 T cell mediated immunity Effects 0.000 description 1
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- 201000005485 Toxoplasmosis Diseases 0.000 description 1
- 241000223104 Trypanosoma Species 0.000 description 1
- 208000037386 Typhoid Diseases 0.000 description 1
- 206010046865 Vaccinia virus infection Diseases 0.000 description 1
- 206010046980 Varicella Diseases 0.000 description 1
- 241000870995 Variola Species 0.000 description 1
- 241000607598 Vibrio Species 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 241000607734 Yersinia <bacteria> Species 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000033289 adaptive immune response Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 208000004631 alopecia areata Diseases 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000006242 amine protecting group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 208000025009 anogenital human papillomavirus infection Diseases 0.000 description 1
- 201000004201 anogenital venereal wart Diseases 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 125000003725 azepanyl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000004305 biphenyl Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229940030156 cell vaccine Drugs 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 201000007241 cutaneous T cell lymphoma Diseases 0.000 description 1
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 description 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- 238000000432 density-gradient centrifugation Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- UJTPZISIAWDGFF-UHFFFAOYSA-N ethenylsulfonylbenzene Chemical compound C=CS(=O)(=O)C1=CC=CC=C1 UJTPZISIAWDGFF-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- 201000009277 hairy cell leukemia Diseases 0.000 description 1
- 208000005252 hepatitis A Diseases 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 230000028996 humoral immune response Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- NSHFLKZNBPJNPA-UHFFFAOYSA-N imidazo[4,5-c]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)N=C3C=NC2=C1 NSHFLKZNBPJNPA-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000037797 influenza A Diseases 0.000 description 1
- 208000037798 influenza B Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000015788 innate immune response Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 208000020082 intraepithelial neoplasia Diseases 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 210000001117 keloid Anatomy 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 230000021633 leukocyte mediated immunity Effects 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000010805 mumps infectious disease Diseases 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- XZTSHUBZWQUAKY-UHFFFAOYSA-N n-[2-(3-chloropropoxy)ethyl]-3-nitroquinolin-4-amine Chemical compound C1=CC=CC2=C(NCCOCCCCl)C([N+](=O)[O-])=CN=C21 XZTSHUBZWQUAKY-UHFFFAOYSA-N 0.000 description 1
- GBMCAEYJLFHDPQ-UHFFFAOYSA-N n-[4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C1=CC=CC2=C(NCC(C)(C)O)C(NC(=O)COC)=CN=C21 GBMCAEYJLFHDPQ-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229940124733 pneumococcal vaccine Drugs 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 201000005404 rubella Diseases 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 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 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- GPTXCAZYUMDUMN-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCO GPTXCAZYUMDUMN-UHFFFAOYSA-N 0.000 description 1
- SXRCKLDJZJXEQW-UHFFFAOYSA-N tert-butyl n-[2-(3-hydroxypropoxy)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCOCCCO SXRCKLDJZJXEQW-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 201000008297 typhoid fever Diseases 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 230000005727 virus proliferation Effects 0.000 description 1
- 125000002256 xylenyl group Chemical group C1(C(C=CC=C1)C)(C)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52677203P | 2003-12-04 | 2003-12-04 | |
| PCT/US2004/040383 WO2005076783A2 (en) | 2003-12-04 | 2004-12-03 | Sulfone substituted imidazo ring ethers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007513170A true JP2007513170A (ja) | 2007-05-24 |
| JP2007513170A5 JP2007513170A5 (enExample) | 2008-01-31 |
Family
ID=34860172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006542750A Pending JP2007513170A (ja) | 2003-12-04 | 2004-12-03 | スルホン置換イミダゾ環エーテル |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7939526B2 (enExample) |
| EP (1) | EP1694674A4 (enExample) |
| JP (1) | JP2007513170A (enExample) |
| CN (1) | CN1914203A (enExample) |
| AR (1) | AR048289A1 (enExample) |
| AU (1) | AU2004315771A1 (enExample) |
| CA (1) | CA2549216A1 (enExample) |
| TW (1) | TW200533352A (enExample) |
| WO (1) | WO2005076783A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11724982B2 (en) | 2014-10-10 | 2023-08-15 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2488801A1 (en) | 2002-06-07 | 2003-12-18 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| AU2004264336B2 (en) | 2003-08-05 | 2010-12-23 | 3M Innovative Properties Company | Formulations containing an immune response modifier |
| AU2004266641A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Oxime substituted imidazo-containing compounds |
| EP1658076B1 (en) | 2003-08-27 | 2013-03-06 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| US20050054665A1 (en) | 2003-09-05 | 2005-03-10 | 3M Innovative Properties Company | Treatment for CD5+ B cell lymphoma |
| ES2544477T3 (es) | 2003-10-03 | 2015-08-31 | 3M Innovative Properties Company | Imidazoquinolinas sustituidas con alcoxi |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| KR20060120069A (ko) | 2003-10-03 | 2006-11-24 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 피라졸로피리딘 및 그의 유사체 |
| JP2007511535A (ja) | 2003-11-14 | 2007-05-10 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドロキシルアミン置換イミダゾ環化合物 |
| US7897767B2 (en) | 2003-11-14 | 2011-03-01 | 3M Innovative Properties Company | Oxime substituted imidazoquinolines |
| RU2409576C2 (ru) | 2003-11-25 | 2011-01-20 | 3М Инновейтив Пропертиз Компани | Системы, содержащие имидазольное кольцо с заместителями, и способы их получения |
| WO2005066170A1 (en) | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| CA2551399A1 (en) | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| EP1730143A2 (en) | 2004-03-24 | 2006-12-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005123080A2 (en) | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| WO2006038923A2 (en) | 2004-06-18 | 2006-04-13 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| WO2006009826A1 (en) | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| PL1789042T3 (pl) | 2004-09-02 | 2012-09-28 | 3M Innovative Properties Co | Układy pierścieni 1-alkoksy 1H-imidazo i sposoby |
| CA2592904C (en) | 2004-12-30 | 2015-04-07 | 3M Innovative Properties Company | Chiral fused [1,2]imidazo[4,5-c] ring compounds |
| US8461174B2 (en) | 2004-12-30 | 2013-06-11 | 3M Innovative Properties Company | Treatment for cutaneous metastases |
| AU2005326708C1 (en) | 2004-12-30 | 2012-08-30 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| US9248127B2 (en) | 2005-02-04 | 2016-02-02 | 3M Innovative Properties Company | Aqueous gel formulations containing immune response modifiers |
| WO2006086449A2 (en) | 2005-02-09 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| JP2008530252A (ja) | 2005-02-09 | 2008-08-07 | コーリー ファーマシューティカル グループ，インコーポレイテッド | オキシムおよびヒドロキシルアミンで置換されたチアゾロ［４，５−ｃ］環化合物ならびに方法 |
| WO2006086634A2 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| WO2006091394A2 (en) | 2005-02-11 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Substituted imidazoquinolines and imidazonaphthyridines |
| EP1851218A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
| EP1851220A2 (en) * | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazonaphthyridines |
| JP2008538203A (ja) | 2005-02-23 | 2008-10-16 | コーリー ファーマシューティカル グループ，インコーポレイテッド | インターフェロンの生合成を優先的に誘導する方法 |
| WO2006098852A2 (en) | 2005-02-23 | 2006-09-21 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinolines |
| US7943610B2 (en) | 2005-04-01 | 2011-05-17 | 3M Innovative Properties Company | Pyrazolopyridine-1,4-diamines and analogs thereof |
| AU2006232375A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| EA200800782A1 (ru) | 2005-09-09 | 2008-08-29 | Коли Фармасьютикал Груп, Инк. | ПРОИЗВОДНЫЕ АМИДА И КАРБАМАТА N-{2-[4-АМИНО-2-(ЭТОКСИМЕТИЛ)-1Н-ИМИДАЗОЛО[4,5-c]ХИНОЛИН-1-IL]-1,1-ДИМЕТИЛЭТИЛ}МЕТАНСУЛЬФОНАМИДА И СПОСОБЫ |
| ZA200803029B (en) | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
| US20090240055A1 (en) * | 2005-09-23 | 2009-09-24 | Krepski Larry R | Method for 1H-Imidazo[4,5-C] Pyridines and Analogs Thereof |
| WO2007056112A2 (en) | 2005-11-04 | 2007-05-18 | Coley Pharmaceutical Group, Inc. | Hydroxy and alkoxy substituted 1h-imidazoquinolines and methods |
| WO2007075468A1 (en) * | 2005-12-16 | 2007-07-05 | Coley Pharmaceutical Group, Inc. | Substituted imidazoquinolines, imidazonaphthyridines, and imidazopyridines, compositions, and methods |
| WO2007100634A2 (en) | 2006-02-22 | 2007-09-07 | 3M Innovative Properties Company | Immune response modifier conjugates |
| US8329721B2 (en) | 2006-03-15 | 2012-12-11 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1H-imidazonaphthyridines and methods |
| US7906506B2 (en) | 2006-07-12 | 2011-03-15 | 3M Innovative Properties Company | Substituted chiral fused [1,2] imidazo [4,5-c] ring compounds and methods |
| WO2008030511A2 (en) | 2006-09-06 | 2008-03-13 | Coley Pharmaceuticial Group, Inc. | Substituted 3,4,6,7-tetrahydro-5h, 1,2a,4a,8-tetraazacyclopenta[cd]phenalenes |
| US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
| HRP20170433T1 (hr) | 2010-08-17 | 2017-05-05 | 3M Innovative Properties Company | Pripravci spoja za izmjenu lipidiranog imunološkog odgovora, formulacije, i postupci |
| CN103582496B (zh) | 2011-06-03 | 2016-05-11 | 3M创新有限公司 | 具有聚乙二醇链段的异双官能连接基以及由其制成的免疫应答调节剂缀合物 |
| WO2012167081A1 (en) | 2011-06-03 | 2012-12-06 | 3M Innovative Properties Company | Hydrazino 1h-imidazoquinolin-4-amines and conjugates made therefrom |
| CN105025854A (zh) | 2013-01-07 | 2015-11-04 | 宾夕法尼亚大学董事会 | 治疗皮肤t细胞淋巴瘤的组合物和方法 |
| ES2804101T3 (es) * | 2014-04-22 | 2021-02-03 | Hoffmann La Roche | Compuestos de 4-amino-imidazoquinolina |
| PT3265458T (pt) | 2015-03-06 | 2019-02-13 | Hoffmann La Roche | Compostos de dicarboxamida de benzazepina |
| US10526309B2 (en) | 2015-10-02 | 2020-01-07 | The University Of North Carolina At Chapel Hill | Pan-TAM inhibitors and Mer/Axl dual inhibitors |
| US10533007B2 (en) | 2016-04-19 | 2020-01-14 | Innate Tumor Immunity, Inc. | NLRP3 modulators |
| MX2018012249A (es) | 2016-04-19 | 2019-02-07 | Innate Tumor Immunity Inc | Moduladores de nlpr3. |
| JP7022702B2 (ja) | 2016-05-23 | 2022-02-18 | エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト | 第二級アミド基を有するベンズアゼピンジカルボキサミド化合物 |
| JP6918838B2 (ja) | 2016-05-23 | 2021-08-11 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | 第三級アミド基を有するベンズアゼピンジカルボキサミド化合物 |
| WO2017216054A1 (en) | 2016-06-12 | 2017-12-21 | F. Hoffmann-La Roche Ag | Dihydropyrimidinyl benzazepine carboxamide compounds |
| TWI674261B (zh) | 2017-02-17 | 2019-10-11 | 美商英能腫瘤免疫股份有限公司 | Nlrp3 調節劑 |
| EP3728255B1 (en) | 2017-12-20 | 2022-01-26 | 3M Innovative Properties Company | Amide substituted imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
| KR20200128116A (ko) | 2018-02-28 | 2020-11-11 | 화이자 인코포레이티드 | Il-15 변이체 및 이의 용도 |
| KR20230146098A (ko) | 2018-05-23 | 2023-10-18 | 화이자 인코포레이티드 | GUCY2c에 특이적인 항체 및 이의 용도 |
| DK3797121T3 (da) | 2018-05-23 | 2024-07-08 | Pfizer | Antistoffer, der er specifikke for CD3, og anvendelser deraf |
| WO2020128893A1 (en) | 2018-12-21 | 2020-06-25 | Pfizer Inc. | Combination treatments of cancer comprising a tlr agonist |
| PE20230160A1 (es) | 2019-12-17 | 2023-02-01 | Pfizer | Anticuerpos especificos para cd47, pd-l1 y sus usos |
| JP2023533793A (ja) | 2020-07-17 | 2023-08-04 | ファイザー・インク | 治療用抗体およびそれらの使用 |
| GB202213166D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
| WO2025104289A1 (en) | 2023-11-17 | 2025-05-22 | Medincell S.A. | Antineoplastic combinations |
Family Cites Families (98)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US664260A (en) * | 1897-09-29 | 1900-12-18 | William Hamlin | Manufacture of starch. |
| US660747A (en) * | 1900-05-31 | 1900-10-30 | Bausch & Lomb | Objective. |
| US3314941A (en) | 1964-06-23 | 1967-04-18 | American Cyanamid Co | Novel substituted pyridodiazepins |
| IL73534A (en) | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| ZA848968B (en) | 1983-11-18 | 1986-06-25 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines |
| US5238944A (en) | 1988-12-15 | 1993-08-24 | Riker Laboratories, Inc. | Topical formulations and transdermal delivery systems containing 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine |
| US5756747A (en) | 1989-02-27 | 1998-05-26 | Riker Laboratories, Inc. | 1H-imidazo 4,5-c!quinolin-4-amines |
| US5037986A (en) | 1989-03-23 | 1991-08-06 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo[4,5-c]quinolin-4-amines |
| US4929624A (en) | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo(4,5-c)quinolin-4-amines |
| NZ232740A (en) | 1989-04-20 | 1992-06-25 | Riker Laboratories Inc | Solution for parenteral administration comprising a 1h-imidazo(4,5-c) quinolin-4-amine derivative, an acid and a tonicity adjuster |
| US4988815A (en) | 1989-10-26 | 1991-01-29 | Riker Laboratories, Inc. | 3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines |
| ATE121088T1 (de) | 1990-10-05 | 1995-04-15 | Minnesota Mining & Mfg | Verfahren zur herstellung von imidazo(4,5- c>chinolin-4-aminen. |
| US5389640A (en) | 1991-03-01 | 1995-02-14 | Minnesota Mining And Manufacturing Company | 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US5175296A (en) | 1991-03-01 | 1992-12-29 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]quinolin-4-amines and processes for their preparation |
| US5268376A (en) | 1991-09-04 | 1993-12-07 | Minnesota Mining And Manufacturing Company | 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US5266575A (en) | 1991-11-06 | 1993-11-30 | Minnesota Mining And Manufacturing Company | 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines |
| IL105325A (en) | 1992-04-16 | 1996-11-14 | Minnesota Mining & Mfg | Immunogen/vaccine adjuvant composition |
| US5395937A (en) | 1993-01-29 | 1995-03-07 | Minnesota Mining And Manufacturing Company | Process for preparing quinoline amines |
| CA2167042A1 (en) | 1993-07-15 | 1995-01-26 | Kyle J. Lindstrom | Imidazo[4,5-c]pyridin-4-amines |
| US5352784A (en) | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| US5482936A (en) | 1995-01-12 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-C]quinoline amines |
| JPH09208584A (ja) | 1996-01-29 | 1997-08-12 | Terumo Corp | アミド誘導体、およびそれを含有する医薬製剤、および合成中間体 |
| US5693811A (en) | 1996-06-21 | 1997-12-02 | Minnesota Mining And Manufacturing Company | Process for preparing tetrahdroimidazoquinolinamines |
| US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| CZ294563B6 (cs) | 1996-10-25 | 2005-02-16 | Minnesota Mining And Manufacturing Company | Sloučeniny představující modifikátory imunitní odezvy při léčení nemocí mediovaných TH2 buňkami a nemocí odvozených |
| US5939090A (en) | 1996-12-03 | 1999-08-17 | 3M Innovative Properties Company | Gel formulations for topical drug delivery |
| US6069149A (en) | 1997-01-09 | 2000-05-30 | Terumo Kabushiki Kaisha | Amide derivatives and intermediates for the synthesis thereof |
| US6446153B2 (en) * | 1997-03-14 | 2002-09-03 | Intel Corporation | Shared embedded microcontroller interface |
| JPH1180156A (ja) | 1997-09-04 | 1999-03-26 | Hokuriku Seiyaku Co Ltd | １−（置換アリール）アルキル−１ｈ−イミダゾピリジン−４−アミン誘導体 |
| UA67760C2 (uk) | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
| JPH11222432A (ja) | 1998-02-03 | 1999-08-17 | Terumo Corp | インターフェロンを誘起するアミド誘導体を含有する外用剤 |
| US6569104B2 (en) * | 1998-07-16 | 2003-05-27 | Canon Kabushiki Kaisha | Blood vessel detecting apparatus |
| US6110929A (en) | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| JP2000119271A (ja) | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | １ｈ―イミダゾピリジン誘導体 |
| SK287112B6 (sk) | 1999-01-08 | 2009-12-07 | 3M Innovative Properties Company | Použitie zlúčeniny modifikujúcej imunitnú odpoveď pri liečení cervikálnej dysplázie |
| US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| US6558951B1 (en) | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| JP2000247884A (ja) | 1999-03-01 | 2000-09-12 | Sumitomo Pharmaceut Co Ltd | アラキドン酸誘発皮膚疾患治療剤 |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6451810B1 (en) | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6331539B1 (en) | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| CA2306170A1 (en) * | 2000-04-18 | 2001-10-18 | Kenneth Curry | Novel amino, carboxy derivatives of barbituric acid |
| US20020055517A1 (en) | 2000-09-15 | 2002-05-09 | 3M Innovative Properties Company | Methods for delaying recurrence of herpes virus symptoms |
| JP2002145777A (ja) | 2000-11-06 | 2002-05-22 | Sumitomo Pharmaceut Co Ltd | アラキドン酸誘発皮膚疾患治療剤 |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US6664260B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Heterocyclic ether substituted imidazoquinolines |
| US6667312B2 (en) | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| UA75622C2 (en) | 2000-12-08 | 2006-05-15 | 3M Innovative Properties Co | Aryl ether substituted imidazoquinolines, pharmaceutical composition based thereon |
| US6677348B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| US6660747B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| US6677347B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| WO2002046749A2 (en) | 2000-12-08 | 2002-06-13 | 3M Innovative Properties Company | Screening method for identifying compounds that selectively induce interferon alpha |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| US6664265B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6660735B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| US20020107262A1 (en) | 2000-12-08 | 2002-08-08 | 3M Innovative Properties Company | Substituted imidazopyridines |
| US6664264B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US7226928B2 (en) * | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
| JP2005501550A (ja) | 2001-08-30 | 2005-01-20 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫反応調整剤分子を用いた形質細胞様樹状細胞を成熟させる方法 |
| ATE511840T1 (de) | 2001-10-09 | 2011-06-15 | Amgen Inc | Imidazolderivate als entzündungshemmende mittel |
| EP1478371A4 (en) | 2001-10-12 | 2007-11-07 | Univ Iowa Res Found | METHOD AND PRODUCTS FOR IMPROVING IMMUNE RESPONSES WITH IMIDAZOCHINOLINE COMPOUNDS |
| AU2002343728A1 (en) | 2001-11-16 | 2003-06-10 | 3M Innovative Properties Company | Methods and compositions related to irm compounds and toll-like receptor pathways |
| EP1450804B9 (en) | 2001-11-29 | 2009-04-01 | 3M Innovative Properties Company | Pharmaceutical formulations comprising an immune response modifier |
| US6677349B1 (en) | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| EP1478327B1 (en) | 2002-02-22 | 2015-04-29 | Meda AB | Method of reducing and treating uvb-induced immunosuppression |
| GB0211649D0 (en) | 2002-05-21 | 2002-07-03 | Novartis Ag | Organic compounds |
| WO2003101949A2 (en) | 2002-05-29 | 2003-12-11 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| CA2488801A1 (en) | 2002-06-07 | 2003-12-18 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| ES2271650T3 (es) | 2002-07-23 | 2007-04-16 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Preparacion de 1h-imidazo (4,5-c) quinolin-4-aminas mediante los productos intermedios de 1h-imidazo (4,5-c) quinolin-4-ftalimida. |
| DE60312701T8 (de) | 2002-07-26 | 2008-08-21 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Darstellung von 1h-imidazo[4,5-c]chinolin-4-aminen über neue 1h-imidazo[4,5-c] chinolin-4-cyano- und 1h-imidazo[4,5-c]chinolin-4-carboxamid intermediate |
| DK1545597T3 (da) | 2002-08-15 | 2011-01-31 | 3M Innovative Properties Co | Immunstimulerende sammensætninger og fremgangsmåde til stimulering af en immunrespons |
| US6818650B2 (en) | 2002-09-26 | 2004-11-16 | 3M Innovative Properties Company | 1H-imidazo dimers |
| AU2003287316A1 (en) | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Assays relating to toll-like receptor activity |
| AU2003287324A1 (en) | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Gene expression systems and recombinant cell lines |
| NZ540826A (en) | 2002-12-20 | 2008-07-31 | 3M Innovative Properties Co | Aryl / hetaryl substituted imidazoquinolines |
| EP2572715A1 (en) | 2002-12-30 | 2013-03-27 | 3M Innovative Properties Company | Immunostimulatory Combinations |
| JP2006517974A (ja) | 2003-02-13 | 2006-08-03 | スリーエム イノベイティブ プロパティズ カンパニー | Ｉｒｍ化合物およびトル様受容体８に関する方法および組成物 |
| WO2004075865A2 (en) | 2003-02-27 | 2004-09-10 | 3M Innovative Properties Company | Selective modulation of tlr-mediated biological activity |
| CA2517528A1 (en) | 2003-03-04 | 2004-09-16 | 3M Innovative Properties Company | Prophylactic treatment of uv-induced epidermal neoplasia |
| JP2006519877A (ja) | 2003-03-07 | 2006-08-31 | スリーエム イノベイティブ プロパティズ カンパニー | １−アミノ１ｈ−イミダゾキノリン |
| CA2518282C (en) | 2003-03-13 | 2012-11-06 | 3M Innovative Properties Company | Methods of improving skin quality |
| JP2006523212A (ja) | 2003-03-13 | 2006-10-12 | スリーエム イノベイティブ プロパティズ カンパニー | 皮膚病変の診断方法 |
| US7179253B2 (en) | 2003-03-13 | 2007-02-20 | 3M Innovative Properties Company | Method of tattoo removal |
| JP4139251B2 (ja) * | 2003-03-17 | 2008-08-27 | 本田技研工業株式会社 | 電動管理機 |
| EP1613956A2 (en) | 2003-03-25 | 2006-01-11 | 3M Innovative Properties Company | Selective activation of cellular activities mediated through a common toll-like receptor |
| US20040192585A1 (en) | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
| EP1615665A4 (en) | 2003-04-10 | 2010-10-06 | 3M Innovative Properties Co | DISTRIBUTION OF THE IMMUNE RESPONSE MODIFYING LINKS |
| US20040214851A1 (en) | 2003-04-28 | 2004-10-28 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
| AU2004266641A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Oxime substituted imidazo-containing compounds |
| WO2005018555A2 (en) | 2003-08-14 | 2005-03-03 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
| CA2537450C (en) | 2003-09-05 | 2012-04-17 | Anadys Pharmaceuticals, Inc. | Administration of tlr7 ligands and prodrugs thereof for treatment of infection by hepatitis c virus |
| EP1668010A2 (en) | 2003-10-01 | 2006-06-14 | Taro Pharmaceuticals U.S.A., Inc. | Method of preparing 4-amino-1h -imidazo(4,5- c )quinolines and acid addition salts thereof |
| ITMI20032121A1 (it) | 2003-11-04 | 2005-05-05 | Dinamite Dipharma Spa In Forma Abbr Eviata Dipharm | Procedimento per la preparazione di imiquimod e suoi intermedi |
-
2004
- 2004-12-03 CA CA002549216A patent/CA2549216A1/en not_active Abandoned
- 2004-12-03 EP EP04821353A patent/EP1694674A4/en not_active Withdrawn
- 2004-12-03 CN CNA2004800414001A patent/CN1914203A/zh active Pending
- 2004-12-03 JP JP2006542750A patent/JP2007513170A/ja active Pending
- 2004-12-03 WO PCT/US2004/040383 patent/WO2005076783A2/en not_active Ceased
- 2004-12-03 TW TW093137541A patent/TW200533352A/zh unknown
- 2004-12-03 US US10/596,117 patent/US7939526B2/en not_active Expired - Fee Related
- 2004-12-03 AU AU2004315771A patent/AU2004315771A1/en not_active Abandoned
- 2004-12-03 AR ARP040104518A patent/AR048289A1/es unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11724982B2 (en) | 2014-10-10 | 2023-08-15 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005076783A3 (en) | 2005-12-29 |
| US7939526B2 (en) | 2011-05-10 |
| TW200533352A (en) | 2005-10-16 |
| US20070155767A1 (en) | 2007-07-05 |
| CA2549216A1 (en) | 2005-08-25 |
| AR048289A1 (es) | 2006-04-19 |
| EP1694674A2 (en) | 2006-08-30 |
| CN1914203A (zh) | 2007-02-14 |
| WO2005076783A2 (en) | 2005-08-25 |
| EP1694674A4 (en) | 2010-07-07 |
| AU2004315771A1 (en) | 2005-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7939526B2 (en) | Sulfone substituted imidazo ring ethers | |
| JP5128940B2 (ja) | 置換イミダゾキノリン、イミダゾピリジン、およびイミダゾナフチリジン | |
| US8343993B2 (en) | Hydroxyalkyl substituted imidazonaphthyridines | |
| JP5247458B2 (ja) | ヒドロキシ及びアルコキシ置換１ｈ−イミダゾキノリン及び方法 | |
| US8802853B2 (en) | Arylalkenyl and arylalkynyl substituted imidazoquinolines | |
| US20070259907A1 (en) | Aryl and arylalkylenyl substituted thiazoloquinolines and thiazolonaphthyridines | |
| WO2006091647A2 (en) | Method of preferentially inducing the biosynthesis of interferon | |
| AU2006223634A1 (en) | Hydroxyalkyl substituted imidazoquinolines | |
| WO2005123079A2 (en) | Urea substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines | |
| EP1851218A2 (en) | Hydroxyalkyl substituted imidazoquinoline compounds and methods | |
| JP2008511683A (ja) | ２−アミノ１ｈ−イミダゾ環構造および方法 | |
| WO2005123080A2 (en) | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines | |
| AU2003301052A1 (en) | Aryl / hetaryl substituted imidazoquinolines | |
| WO2006009826A1 (en) | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines | |
| JP2007517044A (ja) | イミダゾキノリニル、イミダゾピリジニル、およびイミダゾナフチリジニルスルホンアミド | |
| US9938275B2 (en) | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20071129 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20071129 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110426 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20111004 |