AU2004293096A1 - Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines - Google Patents
Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines Download PDFInfo
- Publication number
- AU2004293096A1 AU2004293096A1 AU2004293096A AU2004293096A AU2004293096A1 AU 2004293096 A1 AU2004293096 A1 AU 2004293096A1 AU 2004293096 A AU2004293096 A AU 2004293096A AU 2004293096 A AU2004293096 A AU 2004293096A AU 2004293096 A1 AU2004293096 A1 AU 2004293096A1
- Authority
- AU
- Australia
- Prior art keywords
- group
- alkyl
- aryl
- heteroaryl
- alkylene
- 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.)
- Abandoned
Links
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title description 18
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 4
- VFTLXHXYGQSOEN-UHFFFAOYSA-N 1h-imidazo[4,5-b][1,8]naphthyridine Chemical class C1=CN=C2NC3=NC=NC3=CC2=C1 VFTLXHXYGQSOEN-UHFFFAOYSA-N 0.000 title description 2
- 150000005232 imidazopyridines Chemical class 0.000 title description 2
- 125000003544 oxime group Chemical group 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 279
- 125000003118 aryl group Chemical group 0.000 claims description 181
- 125000001072 heteroaryl group Chemical group 0.000 claims description 175
- 150000001875 compounds Chemical class 0.000 claims description 169
- -1 heteroarylalkylenyl Chemical group 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 127
- 239000001257 hydrogen Substances 0.000 claims description 124
- 125000003342 alkenyl group Chemical group 0.000 claims description 121
- 125000000623 heterocyclic group Chemical group 0.000 claims description 114
- 150000003839 salts Chemical class 0.000 claims description 93
- 229910052736 halogen Inorganic materials 0.000 claims description 85
- 229920006395 saturated elastomer Polymers 0.000 claims description 85
- 125000003545 alkoxy group Chemical group 0.000 claims description 83
- 150000002367 halogens Chemical class 0.000 claims description 82
- 125000002947 alkylene group Chemical group 0.000 claims description 77
- 125000001188 haloalkyl group Chemical group 0.000 claims description 75
- 125000001424 substituent group Chemical group 0.000 claims description 75
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 74
- 125000005466 alkylenyl group Chemical group 0.000 claims description 67
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 60
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 60
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 59
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 58
- 125000004414 alkyl thio group Chemical group 0.000 claims description 53
- 125000000304 alkynyl group Chemical group 0.000 claims description 50
- 125000004450 alkenylene group Chemical group 0.000 claims description 49
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000000732 arylene group Chemical group 0.000 claims description 37
- 125000005549 heteroarylene group Chemical group 0.000 claims description 36
- 125000004419 alkynylene group Chemical group 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 30
- 125000004104 aryloxy group Chemical group 0.000 claims description 30
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 241001465754 Metazoa Species 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 201000010099 disease Diseases 0.000 claims description 25
- 125000004122 cyclic group Chemical group 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 15
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 230000003612 virological effect Effects 0.000 claims description 10
- 230000001613 neoplastic effect Effects 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 230000002452 interceptive effect Effects 0.000 claims description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 230000001939 inductive effect Effects 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 108010011222 cyclo(Arg-Pro) Proteins 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 230000001419 dependent effect Effects 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 claims 1
- VQEKJSSQZKIVQF-UHFFFAOYSA-N NS=O Chemical compound NS=O VQEKJSSQZKIVQF-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 511
- 238000006243 chemical reaction Methods 0.000 description 298
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 225
- 239000000243 solution Substances 0.000 description 172
- 230000002829 reductive effect Effects 0.000 description 155
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 143
- 239000011541 reaction mixture Substances 0.000 description 138
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 132
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 111
- 239000000203 mixture Substances 0.000 description 109
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 102
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 84
- 239000007787 solid Substances 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
- 229910001868 water Inorganic materials 0.000 description 76
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 71
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 70
- 235000017557 sodium bicarbonate Nutrition 0.000 description 70
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 67
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- 238000007429 general method Methods 0.000 description 47
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 47
- 239000000047 product Substances 0.000 description 47
- 238000007796 conventional method Methods 0.000 description 46
- 239000010410 layer Substances 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 44
- 239000000463 material Substances 0.000 description 43
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 42
- 235000019341 magnesium sulphate Nutrition 0.000 description 42
- 239000002904 solvent Substances 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 38
- 238000000746 purification Methods 0.000 description 34
- 239000012044 organic layer Substances 0.000 description 32
- 239000003921 oil Substances 0.000 description 31
- 235000019198 oils Nutrition 0.000 description 31
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- 238000001953 recrystallisation Methods 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- 229910000027 potassium carbonate Inorganic materials 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 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 25
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 25
- 239000000908 ammonium hydroxide Substances 0.000 description 25
- 239000012267 brine Substances 0.000 description 23
- 239000000843 powder Substances 0.000 description 23
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
- 102000004127 Cytokines Human genes 0.000 description 22
- 108090000695 Cytokines Proteins 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 238000003818 flash chromatography Methods 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- 239000012071 phase Substances 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 229910052938 sodium sulfate Inorganic materials 0.000 description 19
- 235000011152 sodium sulphate Nutrition 0.000 description 19
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 18
- 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 18
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 16
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 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 14
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 14
- 230000009467 reduction Effects 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- JAFMOTJMRSZOJE-UHFFFAOYSA-N 1,1,1-trimethoxybutane Chemical compound CCCC(OC)(OC)OC JAFMOTJMRSZOJE-UHFFFAOYSA-N 0.000 description 12
- HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical class NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 description 12
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- 239000013058 crude material Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 12
- 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 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- 238000010828 elution Methods 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 238000010189 synthetic method Methods 0.000 description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 150000002923 oximes Chemical group 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 230000028993 immune response Effects 0.000 description 7
- BMDFNHAUSSAITP-UHFFFAOYSA-N n-methoxybutan-1-imine Chemical compound CCCC=NOC BMDFNHAUSSAITP-UHFFFAOYSA-N 0.000 description 7
- UTOMICFLROGMAE-UHFFFAOYSA-N quinoline-3,4-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CN=C21 UTOMICFLROGMAE-UHFFFAOYSA-N 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical class C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000004795 grignard reagents Chemical class 0.000 description 6
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 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
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 6
- UHUHBFMZVCOEOV-UHFFFAOYSA-N 1h-imidazo[4,5-c]pyridin-4-amine Chemical class NC1=NC=CC2=C1N=CN2 UHUHBFMZVCOEOV-UHFFFAOYSA-N 0.000 description 5
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 5
- QZLAVKQIKWPEEU-UHFFFAOYSA-N 3,4,5,6,10,12-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaene Chemical compound C1=CN2N=NN=C2C2=C1NC=N2 QZLAVKQIKWPEEU-UHFFFAOYSA-N 0.000 description 5
- SJQQWQZOHIXMOO-UHFFFAOYSA-N 4-(2-propylimidazo[4,5-c]quinolin-1-yl)butanal Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC=O)C3=CN=C21 SJQQWQZOHIXMOO-UHFFFAOYSA-N 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 5
- 239000007818 Grignard reagent Substances 0.000 description 5
- 150000001204 N-oxides Chemical class 0.000 description 5
- 235000019502 Orange oil Nutrition 0.000 description 5
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 5
- 102100040247 Tumor necrosis factor Human genes 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001414 amino alcohols Chemical class 0.000 description 5
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 5
- 239000010502 orange oil Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 5
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 238000001665 trituration Methods 0.000 description 5
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 4
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 4
- UJTNVHOFQOMHHY-UHFFFAOYSA-N 1-[4-(methoxyamino)butyl]-2-propylimidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C(N(C(CCC)=N3)CCCCNOC)C3=C(N)N=C21 UJTNVHOFQOMHHY-UHFFFAOYSA-N 0.000 description 4
- LCEBDKLPALDQPV-UHFFFAOYSA-L 1-ethyl-4-(1-ethylpyridin-1-ium-4-yl)pyridin-1-ium;dibromide Chemical compound [Br-].[Br-].C1=C[N+](CC)=CC=C1C1=CC=[N+](CC)C=C1 LCEBDKLPALDQPV-UHFFFAOYSA-L 0.000 description 4
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 4
- RTXYIHGMYDJHEU-UHFFFAOYSA-N 2,4-dichloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=C(Cl)C=CN=C1Cl RTXYIHGMYDJHEU-UHFFFAOYSA-N 0.000 description 4
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PZOXQDQXHVPKMA-UHFFFAOYSA-N 8-nitrotetrazolo[1,5-a]pyridin-7-amine Chemical compound [O-][N+](=O)C1=C(N)C=CN2N=NN=C21 PZOXQDQXHVPKMA-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- QSBWWIXXTMABGJ-UHFFFAOYSA-N [4-(4-amino-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-1-yl)butyl-[(2-methylpropan-2-yl)oxycarbonyl]amino] tert-butyl carbonate Chemical compound N1=C(C)C(C)=C2N(CCCCN(OC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(CCC)=NC2=C1N QSBWWIXXTMABGJ-UHFFFAOYSA-N 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 150000001502 aryl halides Chemical class 0.000 description 4
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- XQXDICZPBIPBPW-UHFFFAOYSA-N ethyl 4-[(3-amino-1,5-naphthyridin-4-yl)amino]butanoate Chemical compound C1=CN=C2C(NCCCC(=O)OCC)=C(N)C=NC2=C1 XQXDICZPBIPBPW-UHFFFAOYSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 4
- 238000011321 prophylaxis Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 230000009385 viral infection Effects 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- SOSHHMMOHSJROY-UHFFFAOYSA-N 1-(4,4-diethoxybutyl)-2-propylimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(OCC)OCC)C3=CN=C21 SOSHHMMOHSJROY-UHFFFAOYSA-N 0.000 description 3
- LIMGILVUVZEMRW-UHFFFAOYSA-N 1-(4-methoxyiminopentyl)-7-phenyl-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC2=C3N(CCCC(C)=NOC)C(CCC)=NC3=C(N)N=C2C=C1C1=CC=CC=C1 LIMGILVUVZEMRW-UHFFFAOYSA-N 0.000 description 3
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 3
- FULSSJUSJYSWAE-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound NC1=NC2=CC=CN=C2C2=C1N=CN2 FULSSJUSJYSWAE-UHFFFAOYSA-N 0.000 description 3
- MTDNQPCBJCWXLQ-UHFFFAOYSA-N 4-n-[2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl]quinoline-3,4-diamine Chemical compound NC=1C=NC2=CC=CC=C2C=1NCC(C)(C)CC1(C)OCCO1 MTDNQPCBJCWXLQ-UHFFFAOYSA-N 0.000 description 3
- APRUZQBKVQKQKI-UHFFFAOYSA-N 5-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)pentan-2-one Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCC(C)=O)C3=C(N)N=C21 APRUZQBKVQKQKI-UHFFFAOYSA-N 0.000 description 3
- QACDDDKHDRLGIV-UHFFFAOYSA-N 5-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]pentan-2-one Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CCCC(C)=O)C3=C(N)N=C21 QACDDDKHDRLGIV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 208000023275 Autoimmune disease Diseases 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 3
- 241000725303 Human immunodeficiency virus Species 0.000 description 3
- 241000725643 Respiratory syncytial virus Species 0.000 description 3
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 3
- 150000003927 aminopyridines Chemical class 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- CXVQSUBJMYZELD-UHFFFAOYSA-N ethyl 4-aminobutanoate;hydrochloride Chemical compound [Cl-].CCOC(=O)CCC[NH3+] CXVQSUBJMYZELD-UHFFFAOYSA-N 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 3
- LZHILKPSYTVLPY-UHFFFAOYSA-N n-methoxy-4-(2-propylimidazo[4,5-c]quinolin-1-yl)butan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCNOC)C3=CN=C21 LZHILKPSYTVLPY-UHFFFAOYSA-N 0.000 description 3
- QKCOMTNUSMORFJ-UHFFFAOYSA-N n-methoxy-n-[4-(2-propylimidazo[4,5-c]quinolin-1-yl)butyl]acetamide Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCN(OC)C(C)=O)C3=CN=C21 QKCOMTNUSMORFJ-UHFFFAOYSA-N 0.000 description 3
- JZECFGCBDZXEPJ-UHFFFAOYSA-N n-methoxy-n-[5-(2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-yl]acetamide Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(C)N(OC)C(C)=O)C3=CN=C21 JZECFGCBDZXEPJ-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- WXBFCJDNQZFOPX-UHFFFAOYSA-N tetrazolo[1,5-a]pyridine-7,8-diamine Chemical compound NC1=C(N)C=CN2N=NN=C21 WXBFCJDNQZFOPX-UHFFFAOYSA-N 0.000 description 3
- KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- FWSXGNXGAJUIPS-WAYWQWQTSA-N (nz)-n-pentan-2-ylidenehydroxylamine Chemical compound CCC\C(C)=N/O FWSXGNXGAJUIPS-WAYWQWQTSA-N 0.000 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 2
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 2
- XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 2
- GFUOIQFPJDKRCI-UHFFFAOYSA-N 1,1-dimethoxybutan-2-amine Chemical compound CCC(N)C(OC)OC GFUOIQFPJDKRCI-UHFFFAOYSA-N 0.000 description 2
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 2
- VGTVXFZXQFIOBG-UHFFFAOYSA-N 1-(2-propylimidazo[4,5-c]quinolin-1-yl)decan-4-one Chemical compound C1=CC=CC2=C3N(CCCC(=O)CCCCCC)C(CCC)=NC3=CN=C21 VGTVXFZXQFIOBG-UHFFFAOYSA-N 0.000 description 2
- ZMJZOCIHQADNJG-UHFFFAOYSA-N 1-(4,4-dimethoxybutyl)-2-(ethoxymethyl)imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C(N(C(COCC)=N3)CCCC(OC)OC)C3=CN=C21 ZMJZOCIHQADNJG-UHFFFAOYSA-N 0.000 description 2
- YJMMOUWAAUTWNR-UHFFFAOYSA-N 1-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)decan-4-one Chemical compound C1=CC=CC2=C3N(CCCC(=O)CCCCCC)C(CCC)=NC3=C(N)N=C21 YJMMOUWAAUTWNR-UHFFFAOYSA-N 0.000 description 2
- RCGNFTFITGAZON-UHFFFAOYSA-N 1-(4-methoxyiminobutyl)-2-methylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCC=NOC)C(C)=NC3=C(N)N=C21 RCGNFTFITGAZON-UHFFFAOYSA-N 0.000 description 2
- JXJORHGRCCODBV-UHFFFAOYSA-N 1-(aminomethyl)cyclopropan-1-ol Chemical compound NCC1(O)CC1 JXJORHGRCCODBV-UHFFFAOYSA-N 0.000 description 2
- UBVWQSAVFBKFFU-UHFFFAOYSA-N 1-[2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl]-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)(C)CC1(C)OCCO1 UBVWQSAVFBKFFU-UHFFFAOYSA-N 0.000 description 2
- JLQRZCVGIQQLCU-UHFFFAOYSA-N 1-[2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl]-2-propylimidazo[4,5-c]quinoline Chemical compound CCCC1=NC2=CN=C3C=CC=CC3=C2N1CC(C)(C)CC1(C)OCCO1 JLQRZCVGIQQLCU-UHFFFAOYSA-N 0.000 description 2
- IRKWBSGRFJXATC-UHFFFAOYSA-N 1-[4-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)butyl]-1-methoxyurea Chemical compound C1=CC=CC2=C3N(CCCCN(OC)C(N)=O)C(C)=NC3=C(N)N=C21 IRKWBSGRFJXATC-UHFFFAOYSA-N 0.000 description 2
- CFCMVEYOSILFRF-UHFFFAOYSA-N 1-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]-1-methoxyurea Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCN(OC)C(N)=O)C3=C(N)N=C21 CFCMVEYOSILFRF-UHFFFAOYSA-N 0.000 description 2
- VPXHYBVMNSCPMN-UHFFFAOYSA-N 1-[4-(methoxyamino)butyl]-2-methylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCNOC)C(C)=NC3=C(N)N=C21 VPXHYBVMNSCPMN-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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IYQGFLYEFXFHJC-UHFFFAOYSA-N 2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)propan-1-amine Chemical compound NCC(C)(C)CC1(C)OCCO1 IYQGFLYEFXFHJC-UHFFFAOYSA-N 0.000 description 2
- CEGLXJGCOGYSFS-UHFFFAOYSA-N 2,4-dichloro-5,6-dimethyl-3-nitropyridine Chemical compound CC1=NC(Cl)=C([N+]([O-])=O)C(Cl)=C1C CEGLXJGCOGYSFS-UHFFFAOYSA-N 0.000 description 2
- RIHSJNLLLHSHAB-UHFFFAOYSA-N 2-(2,2-dimethyl-3-nitropropyl)-2-methyl-1,3-dioxolane Chemical compound [O-][N+](=O)CC(C)(C)CC1(C)OCCO1 RIHSJNLLLHSHAB-UHFFFAOYSA-N 0.000 description 2
- ASFNLQKNVHNFSJ-UHFFFAOYSA-N 2-butyl-1-(4-methoxyimino-4-phenylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCC(=NOC)C1=CC=CC=C1 ASFNLQKNVHNFSJ-UHFFFAOYSA-N 0.000 description 2
- JDZGRQJQHCRAKE-UHFFFAOYSA-N 2-methyl-1-(4-phenylmethoxyiminopentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound CC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCC(C)=NOCC1=CC=CC=C1 JDZGRQJQHCRAKE-UHFFFAOYSA-N 0.000 description 2
- XYJGUYLJPYSNSO-UHFFFAOYSA-N 2-methyl-1-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCC1(C)OCCO1 XYJGUYLJPYSNSO-UHFFFAOYSA-N 0.000 description 2
- HJGDTIGSNPWVFR-UHFFFAOYSA-N 2-methyl-1-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]imidazo[4,5-c]quinoline Chemical compound CC1=NC2=CN=C3C=CC=CC3=C2N1CCCC1(C)OCCO1 HJGDTIGSNPWVFR-UHFFFAOYSA-N 0.000 description 2
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 2
- UBOOKRVGOBKDMM-UHFFFAOYSA-N 3h-imidazo[4,5-c]pyridine Chemical compound C1=NC=C2NC=NC2=C1 UBOOKRVGOBKDMM-UHFFFAOYSA-N 0.000 description 2
- GFLPSABXBDCMCN-UHFFFAOYSA-N 4,4-diethoxybutan-1-amine Chemical compound CCOC(OCC)CCCN GFLPSABXBDCMCN-UHFFFAOYSA-N 0.000 description 2
- TYVAXMOICMBSMT-UHFFFAOYSA-N 4,4-dimethoxybutan-1-amine Chemical compound COC(OC)CCCN TYVAXMOICMBSMT-UHFFFAOYSA-N 0.000 description 2
- HKYNUYYAUZSEKP-UHFFFAOYSA-N 4,4-dimethyl-5-nitropentan-2-one Chemical compound CC(=O)CC(C)(C)C[N+]([O-])=O HKYNUYYAUZSEKP-UHFFFAOYSA-N 0.000 description 2
- GXUJULHTFSYPBR-UHFFFAOYSA-N 4-(2-butyl-5-oxidoimidazo[4,5-c]quinolin-5-ium-1-yl)-1-phenylbutan-1-one Chemical compound CCCCC1=NC2=C[N+]([O-])=C3C=CC=CC3=C2N1CCCC(=O)C1=CC=CC=C1 GXUJULHTFSYPBR-UHFFFAOYSA-N 0.000 description 2
- IVCNUAHMDGBKJV-UHFFFAOYSA-N 4-(2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butanoic acid Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCC(O)=O)C3=CN=C21 IVCNUAHMDGBKJV-UHFFFAOYSA-N 0.000 description 2
- HMTINOWKOAXNCU-UHFFFAOYSA-N 4-(2-propylimidazo[4,5-c][1,5]naphthyridin-1-yl)butanal Chemical compound C1=CC=NC2=C(N(C(CCC)=N3)CCCC=O)C3=CN=C21 HMTINOWKOAXNCU-UHFFFAOYSA-N 0.000 description 2
- ZZPMFMGWOXOYDQ-UHFFFAOYSA-N 4-(4,4-diethoxybutyl)-3H-quinoline-2,4-diamine Chemical compound C(C)OC(CCCC1(CC(=NC2=CC=CC=C12)N)N)OCC ZZPMFMGWOXOYDQ-UHFFFAOYSA-N 0.000 description 2
- WDIZFBONYOHZQR-UHFFFAOYSA-N 4-[(3-nitroquinolin-4-yl)amino]butan-1-ol Chemical compound C1=CC=C2C(NCCCCO)=C([N+]([O-])=O)C=NC2=C1 WDIZFBONYOHZQR-UHFFFAOYSA-N 0.000 description 2
- DGUYOPXSVBCUJH-UHFFFAOYSA-N 4-[(8-amino-5,6-dimethyltetrazolo[1,5-a]pyridin-7-yl)amino]butan-1-ol Chemical compound NC1=C(NCCCCO)C(C)=C(C)N2N=NN=C21 DGUYOPXSVBCUJH-UHFFFAOYSA-N 0.000 description 2
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 2
- UWBCBLMRNYJKQR-UHFFFAOYSA-N 4-n-(4,4-diethoxybutyl)-1,5-naphthyridine-3,4-diamine Chemical compound C1=CN=C2C(NCCCC(OCC)OCC)=C(N)C=NC2=C1 UWBCBLMRNYJKQR-UHFFFAOYSA-N 0.000 description 2
- CZHLCCLPLGIBOO-UHFFFAOYSA-N 4-n-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]quinoline-3,4-diamine Chemical compound NC=1C=NC2=CC=CC=C2C=1NCCCC1(C)OCCO1 CZHLCCLPLGIBOO-UHFFFAOYSA-N 0.000 description 2
- SFJMIDVSYZQCML-UHFFFAOYSA-N 4-n-[4-[tert-butyl(dimethyl)silyl]oxybutyl]quinoline-3,4-diamine Chemical compound C1=CC=C2C(NCCCCO[Si](C)(C)C(C)(C)C)=C(N)C=NC2=C1 SFJMIDVSYZQCML-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WRRHKDJNQFVFAM-UHFFFAOYSA-N 5-(2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCC(C)=O)C3=CN=C21 WRRHKDJNQFVFAM-UHFFFAOYSA-N 0.000 description 2
- NKARDFKHHJKERF-UHFFFAOYSA-N 5-(2-butylimidazo[4,5-c]quinolin-1-yl)pentan-2-ol Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCC(C)O)C3=CN=C21 NKARDFKHHJKERF-UHFFFAOYSA-N 0.000 description 2
- BTYXEBGRORARET-UHFFFAOYSA-N 5-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)-4,4-dimethylpentan-2-one Chemical compound C1=CC=CC2=C3N(CC(C)(C)CC(=O)C)C(C)=NC3=C(N)N=C21 BTYXEBGRORARET-UHFFFAOYSA-N 0.000 description 2
- DXKQNOBQEOHOGH-UHFFFAOYSA-N 5-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)pentan-2-one Chemical compound C1=CC=CC2=C3N(CCCC(=O)C)C(C)=NC3=C(N)N=C21 DXKQNOBQEOHOGH-UHFFFAOYSA-N 0.000 description 2
- OFRAMEYEHQWLKX-UHFFFAOYSA-N 5-(4-amino-7-phenyl-2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-one Chemical compound C1=CC2=C3N(CCCC(C)=O)C(CCC)=NC3=C(N)N=C2C=C1C1=CC=CC=C1 OFRAMEYEHQWLKX-UHFFFAOYSA-N 0.000 description 2
- VRKCNEMUVJCKAJ-UHFFFAOYSA-N 5-(7-bromo-2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-ol Chemical compound C1=C(Br)C=CC2=C(N(C(CCC)=N3)CCCC(C)O)C3=CN=C21 VRKCNEMUVJCKAJ-UHFFFAOYSA-N 0.000 description 2
- SYJZSDWHMAKCHT-UHFFFAOYSA-N 6-methyl-1-(2-propylimidazo[4,5-c]quinolin-1-yl)heptan-4-one Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(=O)CC(C)C)C3=CN=C21 SYJZSDWHMAKCHT-UHFFFAOYSA-N 0.000 description 2
- ZHXHPWDZXNHRME-UHFFFAOYSA-N 7-bromo-4-n-(4,4-dimethoxybutyl)quinoline-3,4-diamine Chemical compound BrC1=CC=C2C(NCCCC(OC)OC)=C(N)C=NC2=C1 ZHXHPWDZXNHRME-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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
- 241000606161 Chlamydia Species 0.000 description 2
- 206010008631 Cholera Diseases 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- 241000709661 Enterovirus Species 0.000 description 2
- 238000003747 Grignard reaction Methods 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
- QLAGBPRMOVOXJX-UHFFFAOYSA-N N-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butoxy]-N-methylhydroxylamine Chemical compound NC1=NC=2C=CC=CC2C2=C1N=C(N2CCCCON(O)C)CCC QLAGBPRMOVOXJX-UHFFFAOYSA-N 0.000 description 2
- VMBNHSDGGKKHIC-UHFFFAOYSA-N N-[5-(4-amino-7-phenyl-2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-yloxy]-N-methylhydroxylamine Chemical compound NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCC(C)ON(O)C)CCC)C2=CC=CC=C2 VMBNHSDGGKKHIC-UHFFFAOYSA-N 0.000 description 2
- AFHATOAFYJFCCE-UHFFFAOYSA-N N-[5-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]pentan-2-yloxy]-N-ethylhydroxylamine Chemical compound NC1=NC=2C=CC=CC2C2=C1N=C(N2CCCC(C)ON(O)CC)COCC AFHATOAFYJFCCE-UHFFFAOYSA-N 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 206010054094 Tumour necrosis Diseases 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 208000003152 Yellow Fever Diseases 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 2
- 229960001171 acetohydroxamic acid Drugs 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 125000004429 atom Chemical group 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
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 125000005620 boronic acid group Chemical class 0.000 description 2
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 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
- 238000001035 drying Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- JTLFMVUOZXASGB-UHFFFAOYSA-N ethyl 4-(2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butanoate Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCC(=O)OCC)C3=CN=C21 JTLFMVUOZXASGB-UHFFFAOYSA-N 0.000 description 2
- NUURJMVDXJVGSL-UHFFFAOYSA-N ethyl 4-(2-propylimidazo[4,5-c]quinolin-1-yl)butanoate Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(=O)OCC)C3=CN=C21 NUURJMVDXJVGSL-UHFFFAOYSA-N 0.000 description 2
- BAJFGOBJUSMHBG-UHFFFAOYSA-N ethyl 4-[(3-aminoquinolin-4-yl)amino]butanoate Chemical compound C1=CC=C2C(NCCCC(=O)OCC)=C(N)C=NC2=C1 BAJFGOBJUSMHBG-UHFFFAOYSA-N 0.000 description 2
- ACGWTYQQQVKRFO-UHFFFAOYSA-N ethyl 4-[(3-nitro-1,5-naphthyridin-4-yl)amino]butanoate Chemical compound C1=CN=C2C(NCCCC(=O)OCC)=C([N+]([O-])=O)C=NC2=C1 ACGWTYQQQVKRFO-UHFFFAOYSA-N 0.000 description 2
- CVZHWHWCSJBQNB-UHFFFAOYSA-N ethyl 4-[(3-nitroquinolin-4-yl)amino]butanoate Chemical compound C1=CC=C2C(NCCCC(=O)OCC)=C([N+]([O-])=O)C=NC2=C1 CVZHWHWCSJBQNB-UHFFFAOYSA-N 0.000 description 2
- BJQUKRMLUVUNAX-UHFFFAOYSA-N ethyl 4-[(5,6-dimethyl-8-nitrotetrazolo[1,5-a]pyridin-7-yl)amino]butanoate Chemical compound [O-][N+](=O)C1=C(NCCCC(=O)OCC)C(C)=C(C)N2N=NN=C21 BJQUKRMLUVUNAX-UHFFFAOYSA-N 0.000 description 2
- LGJQUSLISSCKJT-UHFFFAOYSA-N ethyl 4-[(8-amino-5,6-dimethyltetrazolo[1,5-a]pyridin-7-yl)amino]butanoate Chemical compound NC1=C(NCCCC(=O)OCC)C(C)=C(C)N2N=NN=C21 LGJQUSLISSCKJT-UHFFFAOYSA-N 0.000 description 2
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002443 hydroxylamines Chemical class 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229940047122 interleukins Drugs 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 2
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 2
- LVDIOKLMPLZZGY-UHFFFAOYSA-N n-(4,4-diethoxybutyl)-3-nitro-1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(NCCCC(OCC)OCC)=C([N+]([O-])=O)C=NC2=C1 LVDIOKLMPLZZGY-UHFFFAOYSA-N 0.000 description 2
- DNOMLLQZQULPQE-UHFFFAOYSA-N n-[1-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)-6-methylheptan-4-ylidene]hydroxylamine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(CC(C)C)=NO)C3=C(N)N=C21 DNOMLLQZQULPQE-UHFFFAOYSA-N 0.000 description 2
- AMZGTMZZAUQLLY-UHFFFAOYSA-N n-[4-(4-amino-2-propylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-n-methoxybenzamide Chemical compound CCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCN(OC)C(=O)C1=CC=CC=C1 AMZGTMZZAUQLLY-UHFFFAOYSA-N 0.000 description 2
- SGANQZCDYIVPBL-UHFFFAOYSA-N n-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]-n-methoxyacetamide Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCN(OC)C(C)=O)C3=C(N)N=C21 SGANQZCDYIVPBL-UHFFFAOYSA-N 0.000 description 2
- HSYXKWATTCUKDT-UHFFFAOYSA-N n-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]hydroxylamine;hydrochloride Chemical compound Cl.C1=CC=CC2=C(N(C(CCC)=N3)CCCCNO)C3=C(N)N=C21 HSYXKWATTCUKDT-UHFFFAOYSA-N 0.000 description 2
- VVTLJFVASPTFBL-UHFFFAOYSA-N n-[4-(4-amino-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-1-yl)butyl]-n-hydroxybenzamide Chemical compound CCCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCCN(O)C(=O)C1=CC=CC=C1 VVTLJFVASPTFBL-UHFFFAOYSA-N 0.000 description 2
- KHXHXBSXGBWOJQ-UHFFFAOYSA-N n-[4-(4-amino-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-1-yl)butyl]-n-methoxybenzamide Chemical compound CCCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCCN(OC)C(=O)C1=CC=CC=C1 KHXHXBSXGBWOJQ-UHFFFAOYSA-N 0.000 description 2
- LEMSZRCMNDFGPO-UHFFFAOYSA-N n-methoxy-5-(2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(C)NOC)C3=CN=C21 LEMSZRCMNDFGPO-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
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 2
- 230000001151 other effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- LZMATGARSSLFMQ-UHFFFAOYSA-N propan-2-ylurea Chemical compound CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical class 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 201000010153 skin papilloma Diseases 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- AGOSGCWATIJZHQ-UHFFFAOYSA-N tert-butyl [(2-methylpropan-2-yl)oxycarbonylamino] carbonate Chemical compound CC(C)(C)OC(=O)NOC(=O)OC(C)(C)C AGOSGCWATIJZHQ-UHFFFAOYSA-N 0.000 description 2
- AWLFCLOHTXBKDU-UHFFFAOYSA-N tert-butyl-[4-(2-butylimidazo[4,5-c]quinolin-1-yl)butoxy]-dimethylsilane Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCO[Si](C)(C)C(C)(C)C)C3=CN=C21 AWLFCLOHTXBKDU-UHFFFAOYSA-N 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-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
- 239000003039 volatile agent Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- NMFZTJOPTRNMGL-UHFFFAOYSA-N 1,1-diethoxybutan-2-amine Chemical compound CCOC(OCC)C(N)CC NMFZTJOPTRNMGL-UHFFFAOYSA-N 0.000 description 1
- HYNDYAQJODYUGF-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1NCCCN2CCCC=C21 HYNDYAQJODYUGF-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
- 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
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
- KFAJXZVDBVRZRC-UHFFFAOYSA-N 1,5-naphthyridin-4-amine Chemical class C1=CN=C2C(N)=CC=NC2=C1 KFAJXZVDBVRZRC-UHFFFAOYSA-N 0.000 description 1
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-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
- ZJWANWNTTPLZTH-UHFFFAOYSA-N 1-(4,4-dimethoxybutyl)-2-methylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCC(OC)OC)C(C)=NC3=C(N)N=C21 ZJWANWNTTPLZTH-UHFFFAOYSA-N 0.000 description 1
- BXPLPWTVIDVKDZ-UHFFFAOYSA-N 1-(4,4-dimethoxybutyl)-2-methylimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCC(OC)OC)C(C)=NC3=CN=C21 BXPLPWTVIDVKDZ-UHFFFAOYSA-N 0.000 description 1
- KGHQIRKIFWRXLH-UHFFFAOYSA-N 1-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)-6-methylheptan-4-one Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(=O)CC(C)C)C3=C(N)N=C21 KGHQIRKIFWRXLH-UHFFFAOYSA-N 0.000 description 1
- WUUUIBBTJVOFPT-UHFFFAOYSA-N 1-(4-methoxyimino-2,2-dimethylpentyl)-2-methylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CC(C)(C)CC(C)=NOC)C(C)=NC3=C(N)N=C21 WUUUIBBTJVOFPT-UHFFFAOYSA-N 0.000 description 1
- SVMIVASCMFZNTF-UHFFFAOYSA-N 1-(4-methoxyimino-2,2-dimethylpentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CC(C)(C)CC(C)=NOC)C=NC3=C(N)N=C21 SVMIVASCMFZNTF-UHFFFAOYSA-N 0.000 description 1
- KRBUGTRBIZGMSL-UHFFFAOYSA-N 1-(4-methoxyiminobutyl)-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC=NOC)C3=C(N)N=C21 KRBUGTRBIZGMSL-UHFFFAOYSA-N 0.000 description 1
- RZYQMBJHBNNOTB-UHFFFAOYSA-N 1-(4-methoxyiminopentyl)-2-methylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCC(C)=NOC)C(C)=NC3=C(N)N=C21 RZYQMBJHBNNOTB-UHFFFAOYSA-N 0.000 description 1
- JHESFPDIIYASOL-UHFFFAOYSA-N 1-(4-methoxyiminopentyl)-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-4-amine Chemical compound N1=C(C)C(C)=C2N(CCCC(C)=NOC)C(CCC)=NC2=C1N JHESFPDIIYASOL-UHFFFAOYSA-N 0.000 description 1
- LCSRCPQRSQZJKP-UHFFFAOYSA-N 1-(5-oxido-2-propylimidazo[4,5-c]quinolin-5-ium-1-yl)decan-4-one Chemical compound C1=CC=CC2=C3N(CCCC(=O)CCCCCC)C(CCC)=NC3=C[N+]([O-])=C21 LCSRCPQRSQZJKP-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
- JAESYJIILDGSIM-UHFFFAOYSA-N 1-[2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl]-2-methyl-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound CC1=NC2=C[N+]([O-])=C3C=CC=CC3=C2N1CC(C)(C)CC1(C)OCCO1 JAESYJIILDGSIM-UHFFFAOYSA-N 0.000 description 1
- JKMLGOMHYSMEDW-UHFFFAOYSA-N 1-[2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl]-2-methylimidazo[4,5-c]quinolin-4-amine Chemical compound CC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)(C)CC1(C)OCCO1 JKMLGOMHYSMEDW-UHFFFAOYSA-N 0.000 description 1
- IUBAUEHBIKWHLC-UHFFFAOYSA-N 1-[2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound C1=NC2=C[N+]([O-])=C3C=CC=CC3=C2N1CC(C)(C)CC1(C)OCCO1 IUBAUEHBIKWHLC-UHFFFAOYSA-N 0.000 description 1
- DJQLUTYHBPLBNY-UHFFFAOYSA-N 1-[2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl]imidazo[4,5-c]quinoline Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1CC(C)(C)CC1(C)OCCO1 DJQLUTYHBPLBNY-UHFFFAOYSA-N 0.000 description 1
- MOQCSVXNZVMZKG-UHFFFAOYSA-N 1-[4-(4-amino-2-propylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-1-methoxy-3-propan-2-ylurea Chemical compound C1=CC=NC2=C(N(C(CCC)=N3)CCCCN(OC)C(=O)NC(C)C)C3=C(N)N=C21 MOQCSVXNZVMZKG-UHFFFAOYSA-N 0.000 description 1
- CYTJPLHMTQQBJO-UHFFFAOYSA-N 1-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]-1-hydroxy-3-propan-2-ylurea Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCN(O)C(=O)NC(C)C)C3=C(N)N=C21 CYTJPLHMTQQBJO-UHFFFAOYSA-N 0.000 description 1
- MAAINGGKDDDVAB-UHFFFAOYSA-N 1-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]-1-methoxy-3-phenylurea Chemical compound CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCN(OC)C(=O)NC1=CC=CC=C1 MAAINGGKDDDVAB-UHFFFAOYSA-N 0.000 description 1
- XQBOWTCEKPZFEF-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-1-yl)butyl]-1-hydroxy-3-phenylurea Chemical compound CCCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCCN(O)C(=O)NC1=CC=CC=C1 XQBOWTCEKPZFEF-UHFFFAOYSA-N 0.000 description 1
- MFAGHNJLASAMGM-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-1-yl)butyl]-1-hydroxy-3-propan-2-ylurea Chemical compound N1=C(C)C(C)=C2N(CCCCN(O)C(=O)NC(C)C)C(CCC)=NC2=C1N MFAGHNJLASAMGM-UHFFFAOYSA-N 0.000 description 1
- JKRBPGDKEHROOZ-UHFFFAOYSA-N 1-[5-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-yl]-1-methoxy-3-phenylurea Chemical compound CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCC(C)N(OC)C(=O)NC1=CC=CC=C1 JKRBPGDKEHROOZ-UHFFFAOYSA-N 0.000 description 1
- PSXGSQMOXSWVJB-UHFFFAOYSA-N 1-cyclopentyl-3-methoxyurea Chemical compound CONC(=O)NC1CCCC1 PSXGSQMOXSWVJB-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- MZALFRNTSSLYAZ-UHFFFAOYSA-N 1-ethyl-1-methoxyurea Chemical compound CCN(OC)C(N)=O MZALFRNTSSLYAZ-UHFFFAOYSA-N 0.000 description 1
- BZUZZQAYHNRJPW-UHFFFAOYSA-N 1-methoxy-1-phenylurea Chemical compound CON(C(N)=O)C1=CC=CC=C1 BZUZZQAYHNRJPW-UHFFFAOYSA-N 0.000 description 1
- MBEOKCONJLQHKT-UHFFFAOYSA-N 1-methylimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(C)C=NC3=CN=C21 MBEOKCONJLQHKT-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
- KDXQXHHZOYLQCQ-UHFFFAOYSA-N 2-(ethoxymethyl)-1-(2-methoxyiminobutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(CC)=NOC)C3=C(N)N=C21 KDXQXHHZOYLQCQ-UHFFFAOYSA-N 0.000 description 1
- JFHHEYWDYBREDP-UHFFFAOYSA-N 2-(ethoxymethyl)-1-(4-methoxyiminopentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CCCC(C)=NOC)C3=C(N)N=C21 JFHHEYWDYBREDP-UHFFFAOYSA-N 0.000 description 1
- CREAVZMHRBTEHL-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[4-(methoxyamino)butyl]imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C(N(C(COCC)=N3)CCCCNOC)C3=C(N)N=C21 CREAVZMHRBTEHL-UHFFFAOYSA-N 0.000 description 1
- FGEPRNXUNITOCW-UHFFFAOYSA-N 2-aminobutanal Chemical compound CCC(N)C=O FGEPRNXUNITOCW-UHFFFAOYSA-N 0.000 description 1
- POUXLXXERXMKKM-UHFFFAOYSA-N 2-butyl-1-(4-methoxyiminopentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCC(C)=NOC)C3=C(N)N=C21 POUXLXXERXMKKM-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- WTBWBSOQCBDCAC-UHFFFAOYSA-N 2-methyl-1-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound CC1=NC2=C[N+]([O-])=C3C=CC=CC3=C2N1CCCC1(C)OCCO1 WTBWBSOQCBDCAC-UHFFFAOYSA-N 0.000 description 1
- XUXJHBAJZQREDB-UHFFFAOYSA-N 2-methylbutanamide Chemical compound CCC(C)C(N)=O XUXJHBAJZQREDB-UHFFFAOYSA-N 0.000 description 1
- HMDLTUVOLCTCCS-UHFFFAOYSA-N 2-nitro-1,5-naphthyridine Chemical compound N1=CC=CC2=NC([N+](=O)[O-])=CC=C21 HMDLTUVOLCTCCS-UHFFFAOYSA-N 0.000 description 1
- FMBDGKGJYMSJKF-UHFFFAOYSA-N 2-phenylmethoxypyridine Chemical class C=1C=CC=CC=1COC1=CC=CC=N1 FMBDGKGJYMSJKF-UHFFFAOYSA-N 0.000 description 1
- INXCMWOVRDQPDI-UHFFFAOYSA-N 3-(2-methyl-1,3-dioxolan-2-yl)propan-1-amine Chemical compound NCCCC1(C)OCCO1 INXCMWOVRDQPDI-UHFFFAOYSA-N 0.000 description 1
- QPGLUEKHBNOAHG-UHFFFAOYSA-N 3-carboxypropylazanium;chloride Chemical compound Cl.NCCCC(O)=O QPGLUEKHBNOAHG-UHFFFAOYSA-N 0.000 description 1
- ZSUCMDSNISUURZ-UHFFFAOYSA-N 3-ethyl-1-methoxy-1-[5-(2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-yl]urea Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(C)N(OC)C(=O)NCC)C3=CN=C21 ZSUCMDSNISUURZ-UHFFFAOYSA-N 0.000 description 1
- ZWISCKSGNCMAQO-UHFFFAOYSA-N 3-nitro-1H-quinolin-4-one Chemical compound C1=CC=C2C(=O)C([N+](=O)[O-])=CNC2=C1 ZWISCKSGNCMAQO-UHFFFAOYSA-N 0.000 description 1
- BPZZDZZOBAZEPJ-UHFFFAOYSA-N 3-nitro-1h-1,5-naphthyridin-4-one Chemical compound C1=CN=C2C(O)=C([N+]([O-])=O)C=NC2=C1 BPZZDZZOBAZEPJ-UHFFFAOYSA-N 0.000 description 1
- ZXVRNZRQQRBDLX-UHFFFAOYSA-N 3-nitroquinoline Chemical compound C1=CC=CC2=CC([N+](=O)[O-])=CN=C21 ZXVRNZRQQRBDLX-UHFFFAOYSA-N 0.000 description 1
- YDPJFCNFRRNGPD-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,7]naphthyridin-4-amine Chemical class NC1=NC2=CN=CC=C2C2=C1N=CN2 YDPJFCNFRRNGPD-UHFFFAOYSA-N 0.000 description 1
- WERKLTDIRISJFO-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine;hydrochloride Chemical compound Cl.NC1=NC2=CC=CC=C2C2=C1NC=N2 WERKLTDIRISJFO-UHFFFAOYSA-N 0.000 description 1
- FXNUVBIONHYMHY-UHFFFAOYSA-N 4-(2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butanoyl chloride Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCC(Cl)=O)C3=CN=C21 FXNUVBIONHYMHY-UHFFFAOYSA-N 0.000 description 1
- DWESPIANKFPYCY-UHFFFAOYSA-N 4-(2-butylimidazo[4,5-c]quinolin-1-yl)-1-phenylbutan-1-ol Chemical compound CCCCC1=NC2=CN=C3C=CC=CC3=C2N1CCCC(O)C1=CC=CC=C1 DWESPIANKFPYCY-UHFFFAOYSA-N 0.000 description 1
- SHNUMCUORQQDNZ-UHFFFAOYSA-N 4-(2-butylimidazo[4,5-c]quinolin-1-yl)butan-1-ol Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCO)C3=CN=C21 SHNUMCUORQQDNZ-UHFFFAOYSA-N 0.000 description 1
- IGBIYFMZLHXWJJ-UHFFFAOYSA-N 4-(2-butylimidazo[4,5-c]quinolin-1-yl)butanal Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCC=O)C3=CN=C21 IGBIYFMZLHXWJJ-UHFFFAOYSA-N 0.000 description 1
- IUJWNCPACSYRHQ-UHFFFAOYSA-N 4-(2-chloro-5,6-dimethyl-3-nitro-2h-pyridin-1-yl)butan-1-ol Chemical compound CC1=C(C)N(CCCCO)C(Cl)C([N+]([O-])=O)=C1 IUJWNCPACSYRHQ-UHFFFAOYSA-N 0.000 description 1
- BZVREPUTGYTCFI-UHFFFAOYSA-N 4-(4,4-diethoxybutyl)-2-propyl-1h-imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C(NC(CCC)=N3)C3=C(CCCC(OCC)OCC)N=C21 BZVREPUTGYTCFI-UHFFFAOYSA-N 0.000 description 1
- LOSYKNUCWDTEPD-UHFFFAOYSA-N 4-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)-1-phenylbutan-1-one Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCC(=O)C1=CC=CC=C1 LOSYKNUCWDTEPD-UHFFFAOYSA-N 0.000 description 1
- MMXSIURJWJIOFS-UHFFFAOYSA-N 4-(4-amino-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-1-yl)butan-1-ol Chemical compound N1=C(C)C(C)=C2N(CCCCO)C(CCC)=NC2=C1N MMXSIURJWJIOFS-UHFFFAOYSA-N 0.000 description 1
- FEJDQFRIEJTIJX-UHFFFAOYSA-N 4-(7-bromo-2-propylimidazo[4,5-c]quinolin-1-yl)butanal Chemical compound C1=C(Br)C=CC2=C(N(C(CCC)=N3)CCCC=O)C3=CN=C21 FEJDQFRIEJTIJX-UHFFFAOYSA-N 0.000 description 1
- BVQQTLJGWMDQBZ-UHFFFAOYSA-N 4-[(5,6-dimethyl-8-nitrotetrazolo[1,5-a]pyridin-7-yl)amino]butan-1-ol Chemical compound [O-][N+](=O)C1=C(NCCCCO)C(C)=C(C)N2N=NN=C21 BVQQTLJGWMDQBZ-UHFFFAOYSA-N 0.000 description 1
- XXZDQMNZCTWANL-UHFFFAOYSA-N 4-[2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl]-3H-quinoline-3,4-diamine Chemical compound CC(CC1(C(C=NC2=CC=CC=C12)N)N)(CC1(OCCO1)C)C XXZDQMNZCTWANL-UHFFFAOYSA-N 0.000 description 1
- ZYJJNBBFWLQZHN-UHFFFAOYSA-N 4-n-(4,4-diethoxybutyl)quinoline-2,4-diamine Chemical compound C1=CC=C2C(NCCCC(OCC)OCC)=CC(N)=NC2=C1 ZYJJNBBFWLQZHN-UHFFFAOYSA-N 0.000 description 1
- QMTOJARFWRILNR-UHFFFAOYSA-N 4-nitrotetrazolo[1,5-a][1,7]naphthyridine Chemical class [O-][N+](=O)C1=CC2=CC=NC=C2N2C1=NN=N2 QMTOJARFWRILNR-UHFFFAOYSA-N 0.000 description 1
- NDZRXVMRCABYDC-UHFFFAOYSA-N 5-(2-butyl-5-oxidoimidazo[4,5-c]quinolin-5-ium-1-yl)pentan-2-one Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCC(C)=O)C3=C[N+]([O-])=C21 NDZRXVMRCABYDC-UHFFFAOYSA-N 0.000 description 1
- ATVFBCZABQEOQN-UHFFFAOYSA-N 5-(2-butylimidazo[4,5-c]quinolin-1-yl)pentan-2-one Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCC(C)=O)C3=CN=C21 ATVFBCZABQEOQN-UHFFFAOYSA-N 0.000 description 1
- PYRPNQXRDKMSQK-UHFFFAOYSA-N 5-(2-propylimidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one Chemical compound C1=CC=NC2=C(N(C(CCC)=N3)CCCC(C)=O)C3=CN=C21 PYRPNQXRDKMSQK-UHFFFAOYSA-N 0.000 description 1
- SRXLWUMBKDRASI-UHFFFAOYSA-N 5-(2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-ol Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(C)O)C3=CN=C21 SRXLWUMBKDRASI-UHFFFAOYSA-N 0.000 description 1
- NNNFOSKOYVZRDE-UHFFFAOYSA-N 5-(2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-one Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(C)=O)C3=CN=C21 NNNFOSKOYVZRDE-UHFFFAOYSA-N 0.000 description 1
- MJEDARXKYAGMHO-UHFFFAOYSA-N 5-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)-4,4-dimethylpentan-2-one Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CC(C)(C)CC(C)=O)C3=C(N)N=C21 MJEDARXKYAGMHO-UHFFFAOYSA-N 0.000 description 1
- DDRVABYGPQTODO-UHFFFAOYSA-N 5-(4-amino-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-1-yl)pentan-2-one Chemical compound N1=C(C)C(C)=C2N(CCCC(C)=O)C(CCC)=NC2=C1N DDRVABYGPQTODO-UHFFFAOYSA-N 0.000 description 1
- ZXQKQHGORFTJOE-UHFFFAOYSA-N 5-(7-bromo-2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-one Chemical compound C1=C(Br)C=CC2=C(N(C(CCC)=N3)CCCC(C)=O)C3=CN=C21 ZXQKQHGORFTJOE-UHFFFAOYSA-N 0.000 description 1
- YKXPMAVSKVJZDB-UHFFFAOYSA-N 5-(7-phenyl-2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-one Chemical compound C1=CC2=C3N(CCCC(C)=O)C(CCC)=NC3=CN=C2C=C1C1=CC=CC=C1 YKXPMAVSKVJZDB-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
- KABLCOWSEKUDCU-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1CCNC2=C1N=C(N)C1=C2NC=N1 KABLCOWSEKUDCU-UHFFFAOYSA-N 0.000 description 1
- WRNHMDJECJLNGU-UHFFFAOYSA-N 6-methyl-1-(5-oxido-2-propylimidazo[4,5-c]quinolin-5-ium-1-yl)heptan-4-one Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(=O)CC(C)C)C3=C[N+]([O-])=C21 WRNHMDJECJLNGU-UHFFFAOYSA-N 0.000 description 1
- KGTVATADCQABRD-UHFFFAOYSA-N 7-bromo-4-chloro-3-nitroquinoline Chemical compound C1=C(Br)C=CC2=C(Cl)C([N+](=O)[O-])=CN=C21 KGTVATADCQABRD-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
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 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
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
- 208000003950 B-cell lymphoma Diseases 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000589562 Brucella Species 0.000 description 1
- PCYZAWRNOPHTIB-UHFFFAOYSA-N C1=CN2NN=NC2=C2N=CN=C21 Chemical compound C1=CN2NN=NC2=C2N=CN=C21 PCYZAWRNOPHTIB-UHFFFAOYSA-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
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010008263 Cervical dysplasia Diseases 0.000 description 1
- 201000006082 Chickenpox 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
- 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
- 208000001490 Dengue Diseases 0.000 description 1
- 206010012310 Dengue fever Diseases 0.000 description 1
- 241000725619 Dengue virus Species 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 208000004729 Feline Leukemia Diseases 0.000 description 1
- 241000710831 Flavivirus Species 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 241000606790 Haemophilus Species 0.000 description 1
- 241000589989 Helicobacter Species 0.000 description 1
- 241000711549 Hepacivirus C Species 0.000 description 1
- 241000700721 Hepatitis B virus 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 208000002979 Influenza in Birds Diseases 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
- 241000588748 Klebsiella Species 0.000 description 1
- 208000004554 Leishmaniasis Diseases 0.000 description 1
- 241000713666 Lentivirus Species 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 241000186781 Listeria Species 0.000 description 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 201000005505 Measles Diseases 0.000 description 1
- 241000712079 Measles morbillivirus Species 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 108091060294 Messenger RNP Proteins 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 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
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 description 1
- 229910003844 NSO2 Inorganic materials 0.000 description 1
- 241000588653 Neisseria Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241000709664 Picornaviridae Species 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 241000233870 Pneumocystis Species 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 208000000474 Poliomyelitis 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
- 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
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 102220513468 Rhophilin-2_H29N_mutation Human genes 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000006859 Swern oxidation reaction Methods 0.000 description 1
- 230000024932 T cell mediated immunity Effects 0.000 description 1
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
- 102220483118 TLC domain-containing protein 4_H30N_mutation Human genes 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- 201000005485 Toxoplasmosis Diseases 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 208000037386 Typhoid Diseases 0.000 description 1
- 238000010752 Ullmann ether synthesis reaction Methods 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
- 241000607479 Yersinia pestis 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
- PGQZYRQSKYMFOB-UHFFFAOYSA-N [4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl-(2,2-dimethylpropanoyl)amino] tert-butyl carbonate Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCN(OC(=O)OC(C)(C)C)C(=O)C(C)(C)C)C3=C(N)N=C21 PGQZYRQSKYMFOB-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical group 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 208000009621 actinic keratosis Diseases 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 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
- 125000006241 alcohol protecting group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 208000004631 alopecia areata Diseases 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000006242 amine protecting 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
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000001448 anilines 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
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral 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
- 229940121357 antivirals Drugs 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 229940037642 autologous vaccine Drugs 0.000 description 1
- 125000003725 azepanyl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 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
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- NXTYDKDYJFSZSO-UHFFFAOYSA-N butyl-hydroxy-dimethylsilane Chemical compound CCCC[Si](C)(C)O NXTYDKDYJFSZSO-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 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
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940030156 cell vaccine Drugs 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical group 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 description 1
- 238000005660 chlorination reaction Methods 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
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 201000007241 cutaneous T cell lymphoma Diseases 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- CBEYJGNJOCTQGW-UHFFFAOYSA-N cyclopentylurea Chemical compound NC(=O)NC1CCCC1 CBEYJGNJOCTQGW-UHFFFAOYSA-N 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- 208000025729 dengue disease Diseases 0.000 description 1
- 150000004985 diamines Chemical class 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
- 125000005959 diazepanyl group Chemical group 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- LNGNZSMIUVQZOX-UHFFFAOYSA-L disodium;dioxido(sulfanylidene)-$l^{4}-sulfane Chemical compound [Na+].[Na+].[O-]S([O-])=S LNGNZSMIUVQZOX-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- OKVGYBNVJGFTHJ-UHFFFAOYSA-N ethyl 4-(2-propylimidazo[4,5-c][1,5]naphthyridin-1-yl)butanoate Chemical compound C1=CC=NC2=C(N(C(CCC)=N3)CCCC(=O)OCC)C3=CN=C21 OKVGYBNVJGFTHJ-UHFFFAOYSA-N 0.000 description 1
- JSJNTBVGMRVMSG-UHFFFAOYSA-N ethyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butanoate Chemical compound CCOC(=O)CCCNC1=C(C)C(C)=NC(Cl)=C1[N+]([O-])=O JSJNTBVGMRVMSG-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 150000008423 fluorobenzenes Chemical class 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 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 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 201000009277 hairy cell leukemia Diseases 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 208000005252 hepatitis A Diseases 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- SSBVJILJXCVPQD-UHFFFAOYSA-N heptahydrate;hydrochloride Chemical compound O.O.O.O.O.O.O.Cl SSBVJILJXCVPQD-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000028996 humoral immune response Effects 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- RGZRSLKIOCHTSI-UHFFFAOYSA-N hydron;n-methylhydroxylamine;chloride Chemical compound Cl.CNO RGZRSLKIOCHTSI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229940124669 imidazoquinoline Drugs 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
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 238000011065 in-situ storage 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
- 206010022000 influenza Diseases 0.000 description 1
- 208000037797 influenza A Diseases 0.000 description 1
- 208000037798 influenza B Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000015788 innate immune response Effects 0.000 description 1
- 208000020082 intraepithelial neoplasia Diseases 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- CZALJDQHONFVFU-UHFFFAOYSA-N isocyanatocyclopentane Chemical compound O=C=NC1CCCC1 CZALJDQHONFVFU-UHFFFAOYSA-N 0.000 description 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 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
- 208000011379 keloid formation Diseases 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 230000021633 leukocyte mediated immunity Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 229960005037 meningococcal vaccines Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 208000008588 molluscum contagiosum Diseases 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
- 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
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- WAGJAUSVIQMKFH-UHFFFAOYSA-N n-[1-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)decan-4-ylidene]hydroxylamine Chemical compound C1=CC=CC2=C3N(CCCC(CCCCCC)=NO)C(CCC)=NC3=C(N)N=C21 WAGJAUSVIQMKFH-UHFFFAOYSA-N 0.000 description 1
- OOWYPSVQMBEOSY-UHFFFAOYSA-N n-[2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl]-3-nitroquinolin-4-amine Chemical compound [O-][N+](=O)C=1C=NC2=CC=CC=C2C=1NCC(C)(C)CC1(C)OCCO1 OOWYPSVQMBEOSY-UHFFFAOYSA-N 0.000 description 1
- VHNQQOALZSNNNK-UHFFFAOYSA-N n-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]-3-nitroquinolin-4-amine Chemical compound [O-][N+](=O)C=1C=NC2=CC=CC=C2C=1NCCCC1(C)OCCO1 VHNQQOALZSNNNK-UHFFFAOYSA-N 0.000 description 1
- DINSIEZKQBZHSH-UHFFFAOYSA-N n-[4-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)butyl]-n-methoxymethanesulfonamide Chemical compound C1=CC=CC2=C3N(CCCCN(OC)S(C)(=O)=O)C(C)=NC3=C(N)N=C21 DINSIEZKQBZHSH-UHFFFAOYSA-N 0.000 description 1
- PWYKTYFMHPNXMP-UHFFFAOYSA-N n-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]-n-hydroxyacetamide Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCN(O)C(C)=O)C3=C(N)N=C21 PWYKTYFMHPNXMP-UHFFFAOYSA-N 0.000 description 1
- YNLVCIDMLKLIGQ-UHFFFAOYSA-N n-[4-(4-amino-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-1-yl)butyl]-n-hydroxyacetamide Chemical compound N1=C(C)C(C)=C2N(CCCCN(O)C(C)=O)C(CCC)=NC2=C1N YNLVCIDMLKLIGQ-UHFFFAOYSA-N 0.000 description 1
- CXNUPPIYBIEHLS-UHFFFAOYSA-N n-[4-[4-amino-2-(ethoxymethyl)imidazo[4,5-c][1,5]naphthyridin-1-yl]butyl]-n-methoxyacetamide Chemical compound C1=CC=NC2=C(N(C(COCC)=N3)CCCCN(OC)C(C)=O)C3=C(N)N=C21 CXNUPPIYBIEHLS-UHFFFAOYSA-N 0.000 description 1
- OZLZNFISKAPDQT-UHFFFAOYSA-N n-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-3-nitroquinolin-4-amine Chemical compound C1=CC=C2C(NCCCCO[Si](C)(C)C(C)(C)C)=C([N+]([O-])=O)C=NC2=C1 OZLZNFISKAPDQT-UHFFFAOYSA-N 0.000 description 1
- DFYUKJSDZLQDLD-UHFFFAOYSA-N n-[5-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)pentan-2-ylidene]hydroxylamine Chemical compound C1=CC=CC2=C3N(CCCC(C)=NO)C(C)=NC3=C(N)N=C21 DFYUKJSDZLQDLD-UHFFFAOYSA-N 0.000 description 1
- HLIOQFNZIFSKNV-UHFFFAOYSA-N n-[5-(4-amino-2-propylimidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-yl]-n-methoxyacetamide Chemical compound C1=CC=NC2=C(N(C(CCC)=N3)CCCC(C)N(OC)C(C)=O)C3=C(N)N=C21 HLIOQFNZIFSKNV-UHFFFAOYSA-N 0.000 description 1
- LFZHDLQDSVJTPO-UHFFFAOYSA-N n-[5-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]pentan-2-ylidene]hydroxylamine Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CCCC(C)=NO)C3=C(N)N=C21 LFZHDLQDSVJTPO-UHFFFAOYSA-N 0.000 description 1
- FGVAVSPHMIDDFR-UHFFFAOYSA-N n-methoxy-4-(2-propylimidazo[4,5-c][1,5]naphthyridin-1-yl)butan-1-imine Chemical compound C1=CC=NC2=C(N(C(CCC)=N3)CCCC=NOC)C3=CN=C21 FGVAVSPHMIDDFR-UHFFFAOYSA-N 0.000 description 1
- ONOSWMASMJOHLD-UHFFFAOYSA-N n-methoxy-4-(2-propylimidazo[4,5-c]quinolin-1-yl)butan-1-imine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC=NOC)C3=CN=C21 ONOSWMASMJOHLD-UHFFFAOYSA-N 0.000 description 1
- NYERWFSECMAKTQ-UHFFFAOYSA-N n-methoxy-5-(2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-imine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(C)=NOC)C3=CN=C21 NYERWFSECMAKTQ-UHFFFAOYSA-N 0.000 description 1
- PGPJIZPZLAPJPU-UHFFFAOYSA-N n-methoxy-n-methyl-4-(2-propylimidazo[4,5-c]quinolin-1-yl)butanamide Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(=O)N(C)OC)C3=CN=C21 PGPJIZPZLAPJPU-UHFFFAOYSA-N 0.000 description 1
- CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-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
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229960001973 pneumococcal vaccines 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
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 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
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 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
- 230000009257 reactivity Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 201000005404 rubella Diseases 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
- 229940075931 sodium dithionate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- FGWRMMTYIZKYMA-UHFFFAOYSA-N tert-butyl-hydroxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O FGWRMMTYIZKYMA-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000001149 thermolysis Methods 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
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 150000003585 thioureas Chemical class 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
- 230000009466 transformation Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JGWFUSVYECJQDT-UHFFFAOYSA-N trimethyl(2-trimethylsilyloxyethoxy)silane Chemical compound C[Si](C)(C)OCCO[Si](C)(C)C JGWFUSVYECJQDT-UHFFFAOYSA-N 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 229960002109 tuberculosis vaccine Drugs 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
- 150000003672 ureas Chemical class 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 230000037314 wound repair Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/10—Antimycotics
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P31/20—Antivirals for DNA viruses
-
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P37/08—Antiallergic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Biotechnology (AREA)
- Hematology (AREA)
- AIDS & HIV (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Otolaryngology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52496103P | 2003-11-25 | 2003-11-25 | |
| US60/524,961 | 2003-11-25 | ||
| US58013904P | 2004-06-16 | 2004-06-16 | |
| US60/580,139 | 2004-06-16 | ||
| US58129304P | 2004-06-18 | 2004-06-18 | |
| US60/581,293 | 2004-06-18 | ||
| PCT/US2004/039673 WO2005051324A2 (en) | 2003-11-25 | 2004-11-24 | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004293096A1 true AU2004293096A1 (en) | 2005-06-09 |
Family
ID=34637184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004293096A Abandoned AU2004293096A1 (en) | 2003-11-25 | 2004-11-24 | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8778963B2 (OSRAM) |
| EP (1) | EP1686992A4 (OSRAM) |
| JP (1) | JP2007512349A (OSRAM) |
| AU (1) | AU2004293096A1 (OSRAM) |
| CA (1) | CA2547085A1 (OSRAM) |
| WO (1) | WO2005051324A2 (OSRAM) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003237386A1 (en) | 2002-06-07 | 2003-12-22 | 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 |
| WO2005018556A2 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| PH12006500401A1 (en) | 2003-08-27 | 2005-03-10 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| EP1660026A4 (en) | 2003-09-05 | 2008-07-16 | 3M Innovative Properties Co | TREATMENT FOR CD5 + B CELL LYMPHOMA |
| CA2540598C (en) | 2003-10-03 | 2013-09-24 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| EP1673087B1 (en) | 2003-10-03 | 2015-05-13 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| EP1685129A4 (en) | 2003-11-14 | 2008-10-22 | 3M Innovative Properties Co | OXIMSUBSTITUTED IMIDAZORING CONNECTIONS |
| WO2005048945A2 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| CA2547020C (en) | 2003-11-25 | 2014-03-25 | 3M Innovative Properties Company | 1h-imidazo[4,5-c]pyridine-4-amine derivatives as immune response modifier |
| US8802853B2 (en) | 2003-12-29 | 2014-08-12 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| WO2005066169A2 (en) | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| AU2005228150A1 (en) * | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| US8017779B2 (en) | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| WO2006038923A2 (en) | 2004-06-18 | 2006-04-13 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| US20070259881A1 (en) * | 2004-06-18 | 2007-11-08 | Dellaria Joseph F Jr | Substituted Imidazo Ring Systems and Methods |
| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| ATE555786T1 (de) | 2004-09-02 | 2012-05-15 | 3M Innovative Properties Co | 1-alkoxy 1h-imidazo-ringsysteme und verfahren |
| WO2007134169A2 (en) * | 2006-05-10 | 2007-11-22 | Nuada, Llc | Indole, benzimidazole, and benzolactam boronic acid compounds, analogs thereof and methods of use thereof |
| AU2005322898B2 (en) | 2004-12-30 | 2011-11-24 | 3M Innovative Properties Company | Chiral fused (1,2)imidazo(4,5-c) ring compounds |
| SI1830876T1 (sl) | 2004-12-30 | 2015-08-31 | Meda Ab | Uporaba imikvimoda za zdravljenje kožnih metastaz, ki izhajajo iz rakavega tumorja dojke |
| JP5313502B2 (ja) | 2004-12-30 | 2013-10-09 | スリーエム イノベイティブ プロパティズ カンパニー | 置換キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| CA2597092A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse 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 |
| AU2006216997A1 (en) | 2005-02-11 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Substituted imidazoquinolines and imidazonaphthyridines |
| CA2597587A1 (en) * | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| WO2006091568A2 (en) * | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazonaphthyridines |
| WO2006091647A2 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Method of preferentially inducing the biosynthesis of interferon |
| US8178677B2 (en) | 2005-02-23 | 2012-05-15 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
| US8158794B2 (en) | 2005-02-23 | 2012-04-17 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
| EP1863814A1 (en) | 2005-04-01 | 2007-12-12 | 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 |
| EP1869043A2 (en) | 2005-04-01 | 2007-12-26 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| AU2006287270A1 (en) | 2005-09-09 | 2007-03-15 | Coley Pharmaceutical Group, Inc. | Amide and carbamate derivatives of N-{2-[4-amino-2- (ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide and methods |
| 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 |
| WO2007035935A1 (en) * | 2005-09-23 | 2007-03-29 | Coley Pharmaceutical Group, Inc. | METHOD FOR 1H-IMIDAZO[4,5-c]PYRIDINES AND ANALOGS THEREOF |
| ES2429170T3 (es) | 2005-11-04 | 2013-11-13 | 3M Innovative Properties Company | 1H-Imidazoquinolinas sustituidas con hidroxilo y alcoxilo y métodos |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 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 |
| WO2008008432A2 (en) | 2006-07-12 | 2008-01-17 | Coley Pharmaceutical Group, Inc. | 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 |
| HRP20131139T1 (hr) | 2008-03-24 | 2014-01-03 | 4Sc Discovery Gmbh | Novi supstituirani imidazokinolini |
| US20110190336A1 (en) * | 2008-10-16 | 2011-08-04 | Cara Therapeutics, Inc. | Azabenzimidazolones |
| EP3222621B1 (en) | 2010-08-17 | 2023-03-08 | 3M Innovative Properties Company | Lipidated immune response modifier compound and its medical use |
| US8728486B2 (en) | 2011-05-18 | 2014-05-20 | University Of Kansas | Toll-like receptor-7 and -8 modulatory 1H imidazoquinoline derived compounds |
| WO2012167088A1 (en) | 2011-06-03 | 2012-12-06 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| EP3366311B1 (en) | 2011-06-03 | 2020-02-26 | 3M Innovative Properties Co. | Hydrazino-1h-imidazoquinolin-4-amines and conjugates made therefrom |
| EP2941233B1 (en) | 2013-01-07 | 2020-10-07 | The Trustees of the University of Pennsylvania | Compositions and methods for treating cutaneous t cell lymphoma |
| KR20150127085A (ko) * | 2013-03-15 | 2015-11-16 | 신젠타 파티서페이션즈 아게 | 살균 활성인 이미다조피리딘 유도체 |
| WO2016057931A1 (en) | 2014-10-10 | 2016-04-14 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
| WO2017184735A1 (en) * | 2016-04-19 | 2017-10-26 | Ifm Therapeutics, Inc | Nlrp3 modulators |
| EP3484518B1 (en) | 2016-07-07 | 2024-08-14 | The Board of Trustees of the Leland Stanford Junior University | Antibody adjuvant conjugates |
| PL3679025T3 (pl) | 2017-09-06 | 2022-07-11 | BioNTech SE | Podstawione imidazochinoliny jako agoniści tlr7 |
| WO2019048036A1 (en) | 2017-09-06 | 2019-03-14 | Biontech Ag | SUBSTITUTED IMIDAZOQUINOLINES |
| CA3086439A1 (en) | 2017-12-20 | 2019-06-27 | 3M Innovative Properties Company | Amide substitued imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
| MX387358B (es) | 2018-02-28 | 2025-03-18 | Pfizer | Variantes de il-15 y usos de las mismas |
| MX2020012607A (es) | 2018-05-23 | 2021-01-29 | Pfizer | Anticuerpos especificos para gucy2c y sus usos. |
| EP3797121B1 (en) | 2018-05-23 | 2024-06-19 | Pfizer Inc. | Antibodies specific for cd3 and uses thereof |
| US20220370606A1 (en) | 2018-12-21 | 2022-11-24 | Pfizer Inc. | Combination Treatments Of Cancer Comprising A TLR Agonist |
| JP7576038B2 (ja) | 2019-03-07 | 2024-10-30 | バイオエヌテック エスエー | 置換イミダゾキノリンの調製方法 |
| JP2022525594A (ja) | 2019-03-15 | 2022-05-18 | ボルト バイオセラピューティクス、インコーポレーテッド | Ｈｅｒ２を標的とする免疫結合体 |
| AU2020410410A1 (en) | 2019-12-17 | 2022-06-09 | Pfizer Inc. | Antibodies specific for CD47, PD-L1, and uses thereof |
| BR112023000701A2 (pt) | 2020-07-17 | 2023-02-07 | Pfizer | Anticorpos terapêuticos e usos dos mesmos |
| WO2025104289A1 (en) | 2023-11-17 | 2025-05-22 | Medincell S.A. | Antineoplastic combinations |
Family Cites Families (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4929624A (en) * | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 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 |
| 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 |
| HU217080B (hu) * | 1990-10-05 | 1999-11-29 | Minnesota Mining And Manufacturing Co. | Új eljárás imidazo[4,5-c]kinolin-4-amin-származékok előállítására |
| 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 |
| FR2673427B1 (fr) * | 1991-03-01 | 1993-06-18 | Sanofi Elf | Derives heterocycliques diazotes n-substitues par un groupement biphenylmethyle, leur preparation, les compositions pharmaceutiques en contenant. |
| 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 |
| EP0708772B1 (en) * | 1993-07-15 | 2000-08-23 | Minnesota Mining And Manufacturing Company | 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 |
| US5935937A (en) * | 1996-06-19 | 1999-08-10 | Fox Chase Cancer Center | Compositions and methods for inducing apoptosis |
| US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| US5693811A (en) * | 1996-06-21 | 1997-12-02 | Minnesota Mining And Manufacturing Company | Process for preparing tetrahdroimidazoquinolinamines |
| US6039969A (en) * | 1996-10-25 | 2000-03-21 | 3M Innovative Properties Company | Immune response modifier compounds for treatment of TH2 mediated and related diseases |
| US5741906A (en) * | 1996-11-15 | 1998-04-21 | Air Products And Chemicals, Inc. | Production of triethylenediamine using surface acidity deactivated zeolite catalysts |
| US5939090A (en) * | 1996-12-03 | 1999-08-17 | 3M Innovative Properties Company | Gel formulations for topical drug delivery |
| EP0894797A4 (en) * | 1997-01-09 | 2001-08-16 | Terumo Corp | NEW AMID DERIVATIVES AND INTERMEDIATES ON YOUR SYNTHESIS |
| 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 |
| 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 |
| US6518280B2 (en) * | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
| US20020058674A1 (en) * | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| EP1140091B1 (en) * | 1999-01-08 | 2005-09-21 | 3M Innovative Properties Company | Formulations comprising imiquimod or other immune response modifiers for treating cervical dysplasia |
| 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 |
| US6573273B1 (en) * | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6451810B1 (en) * | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6541485B1 (en) * | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6376669B1 (en) * | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| DE10001037C1 (de) | 2000-01-13 | 2001-12-13 | Byk Gulden Lomberg Chem Fab | Verfahren und Zwischenprodukte zur Herstellung von Imidazopyridinen |
| US6894060B2 (en) * | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| 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 |
| US6545017B1 (en) * | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6660747B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6660735B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| UA75622C2 (en) * | 2000-12-08 | 2006-05-15 | 3M Innovative Properties Co | Aryl ether substituted imidazoquinolines, pharmaceutical composition based thereon |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6677347B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US6664260B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Heterocyclic ether substituted imidazoquinolines |
| US6545016B1 (en) * | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| AU3249802A (en) * | 2000-12-08 | 2002-06-18 | 3M Innovative Properties Co | 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 |
| US20020107262A1 (en) * | 2000-12-08 | 2002-08-08 | 3M Innovative Properties Company | Substituted imidazopyridines |
| US6677348B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| US6664265B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| MXPA04001972A (es) * | 2001-08-30 | 2005-02-17 | 3M Innovative Properties Co | Metodos para hacer madurar celulas dendricas plasmacitoide utilizando moleculas modificadoras de respuesta enmune. |
| 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 |
| EP1719511B1 (en) * | 2001-11-16 | 2008-12-10 | 3M Innovative Properties Company | N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide, a pharmaceutical composition comprising the same and use thereof |
| WO2004080430A2 (en) * | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Methods of improving skin quality |
| NZ532769A (en) * | 2001-11-29 | 2005-12-23 | 3M Innovative Properties Co | Pharmaceutical formulations comprising an immune response modifier |
| US6677349B1 (en) * | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| SI1478327T1 (sl) * | 2002-02-22 | 2015-08-31 | Meda Ab | Metoda za zmanjšanje in zdravljenje imunosupresije, inducirane z UV-B |
| GB0211649D0 (en) * | 2002-05-21 | 2002-07-03 | Novartis Ag | Organic compounds |
| EP1511746A2 (en) * | 2002-05-29 | 2005-03-09 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| AU2003237386A1 (en) * | 2002-06-07 | 2003-12-22 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| JP2006502121A (ja) * | 2002-07-23 | 2006-01-19 | テバ ジョジセルジャール レースベニュタールシャシャーグ | １Ｈ−イミダゾ［４，５−ｃ］キノリン−４−フタルイミド中間体を介する１Ｈ−イミダゾ−［４，５−ｃ］キノリン−４−アミンの調製 |
| AU2003254221A1 (en) * | 2002-07-26 | 2004-02-16 | Biogal Gyogyszergyar Rt. | Preparation of 1h-imidazo (4,5-c) quinolin-4-amines via novel 1h-imidazo (4,5-c) quinolin-4-cyano and 1h-imidazo (4,5-c) quinolin-4-carboxamide intermediates |
| EP1545597B1 (en) * | 2002-08-15 | 2010-11-17 | 3M Innovative Properties Company | Immunostimulatory compositions and methods of stimulating an immune response |
| WO2004028539A2 (en) * | 2002-09-26 | 2004-04-08 | 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 |
| EP1590348A1 (en) * | 2002-12-20 | 2005-11-02 | 3M Innovative Properties Company | Aryl / hetaryl substituted imidazoquinolines |
| EP2572714A1 (en) * | 2002-12-30 | 2013-03-27 | 3M Innovative Properties Company | Immunostimulatory Combinations |
| EP1592302A4 (en) * | 2003-02-13 | 2007-04-25 | 3M Innovative Properties Co | METHODS AND COMPOSITIONS ASSOCIATED WITH IMMUNE RESPONSE MODIFIER COMPOUNDS AND TOLL-LIKE RECEPTOR 8 |
| WO2004075865A2 (en) * | 2003-02-27 | 2004-09-10 | 3M Innovative Properties Company | Selective modulation of tlr-mediated biological activity |
| US8110582B2 (en) * | 2003-03-04 | 2012-02-07 | 3M Innovative Properties Company | Prophylactic treatment of UV-induced epidermal neoplasia |
| EP1605943A4 (en) * | 2003-03-07 | 2008-01-16 | 3M Innovative Properties Co | 1-AMINO-1H-imidazoquinolines |
| CA2518445A1 (en) * | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Method of tattoo removal |
| 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 |
| JP2006523452A (ja) * | 2003-03-25 | 2006-10-19 | スリーエム イノベイティブ プロパティズ カンパニー | 共通のＴｏｌｌ様受容体を通じて媒介される細胞活性の選択的活性化 |
| US20040192585A1 (en) * | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
| WO2004091500A2 (en) * | 2003-04-10 | 2004-10-28 | 3M Innovative Properties Company | Delivery of immune response modifier compounds |
| WO2004096144A2 (en) * | 2003-04-28 | 2004-11-11 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
| NZ545536A (en) * | 2003-09-05 | 2010-04-30 | Anadys Pharmaceuticals Inc | TLR7 ligands for the treatment of hepatitis C |
| US7687628B2 (en) * | 2003-10-01 | 2010-03-30 | 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
- 2004-11-24 JP JP2006541442A patent/JP2007512349A/ja active Pending
- 2004-11-24 US US10/595,895 patent/US8778963B2/en not_active Expired - Fee Related
- 2004-11-24 WO PCT/US2004/039673 patent/WO2005051324A2/en not_active Ceased
- 2004-11-24 EP EP04812235A patent/EP1686992A4/en not_active Withdrawn
- 2004-11-24 AU AU2004293096A patent/AU2004293096A1/en not_active Abandoned
- 2004-11-24 CA CA002547085A patent/CA2547085A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1686992A2 (en) | 2006-08-09 |
| WO2005051324A3 (en) | 2006-01-05 |
| JP2007512349A (ja) | 2007-05-17 |
| WO2005051324A2 (en) | 2005-06-09 |
| US20070099901A1 (en) | 2007-05-03 |
| CA2547085A1 (en) | 2005-06-09 |
| US8778963B2 (en) | 2014-07-15 |
| EP1686992A4 (en) | 2009-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8778963B2 (en) | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines | |
| EP1687307B1 (en) | Substituted imidazo ring systems and methods | |
| AU2005282726B2 (en) | 1-alkoxy 1H-imidazo ring systems and methods | |
| US8735421B2 (en) | Imidazoquinolinyl sulfonamides | |
| US8802853B2 (en) | Arylalkenyl and arylalkynyl substituted imidazoquinolines | |
| AU2004266658A1 (en) | Hydroxylamine substituted imidazo-containing compounds | |
| AU2004291101A1 (en) | Oxime substituted imidazo ring compounds | |
| AU2004291122A1 (en) | Hydroxylamine substituted imidazo ring compounds | |
| AU2004220534A1 (en) | 1-amino 1H-imidazoquinolines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |