AU2004278014B2 - Alkoxy substituted imidazoquinolines - Google Patents
Alkoxy substituted imidazoquinolines Download PDFInfo
- Publication number
- AU2004278014B2 AU2004278014B2 AU2004278014A AU2004278014A AU2004278014B2 AU 2004278014 B2 AU2004278014 B2 AU 2004278014B2 AU 2004278014 A AU2004278014 A AU 2004278014A AU 2004278014 A AU2004278014 A AU 2004278014A AU 2004278014 B2 AU2004278014 B2 AU 2004278014B2
- Authority
- AU
- Australia
- Prior art keywords
- group
- alkyl
- compound
- alkylene
- salt
- 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.)
- Ceased
Links
- 125000003545 alkoxy group Chemical group 0.000 title claims description 58
- 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 1
- 125000000217 alkyl group Chemical group 0.000 claims description 229
- 229910052739 hydrogen Inorganic materials 0.000 claims description 223
- 150000001875 compounds Chemical class 0.000 claims description 158
- -1 nitro, hydroxy, mercapto Chemical group 0.000 claims description 147
- 125000002947 alkylene group Chemical group 0.000 claims description 140
- 125000003118 aryl group Chemical group 0.000 claims description 119
- 150000003839 salts Chemical class 0.000 claims description 117
- 239000001257 hydrogen Substances 0.000 claims description 104
- 125000000623 heterocyclic group Chemical group 0.000 claims description 100
- 238000000034 method Methods 0.000 claims description 85
- 125000001072 heteroaryl group Chemical group 0.000 claims description 82
- 125000003342 alkenyl group Chemical group 0.000 claims description 70
- 229910052736 halogen Inorganic materials 0.000 claims description 63
- 150000002367 halogens Chemical group 0.000 claims description 63
- 125000004450 alkenylene group Chemical group 0.000 claims description 62
- 125000004419 alkynylene group Chemical group 0.000 claims description 62
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 125000000304 alkynyl group Chemical group 0.000 claims description 42
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000005549 heteroarylene group Chemical group 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 36
- 125000004104 aryloxy group Chemical group 0.000 claims description 36
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 35
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
- 125000000732 arylene group Chemical group 0.000 claims description 34
- 102000004127 Cytokines Human genes 0.000 claims description 30
- 108090000695 Cytokines Proteins 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 241001465754 Metazoa Species 0.000 claims description 28
- 201000010099 disease Diseases 0.000 claims description 28
- 125000001188 haloalkyl group Chemical group 0.000 claims description 28
- 125000003282 alkyl amino group Chemical group 0.000 claims description 26
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 26
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 26
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 26
- 230000015572 biosynthetic process Effects 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 20
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- 230000003612 virological effect Effects 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 230000001613 neoplastic effect Effects 0.000 claims description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 4
- 125000003725 azepanyl group Chemical group 0.000 claims description 4
- 125000004069 aziridinyl group Chemical group 0.000 claims description 4
- 125000005959 diazepanyl group Chemical group 0.000 claims description 4
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 230000001419 dependent effect Effects 0.000 claims 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 424
- 238000006243 chemical reaction Methods 0.000 description 230
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 219
- 239000007787 solid Substances 0.000 description 163
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 156
- 239000000243 solution Substances 0.000 description 154
- 230000002829 reductive effect Effects 0.000 description 143
- 229910052757 nitrogen Inorganic materials 0.000 description 128
- 229910052799 carbon Inorganic materials 0.000 description 121
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 111
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 106
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 106
- 229910001868 water Inorganic materials 0.000 description 106
- 238000005481 NMR spectroscopy Methods 0.000 description 103
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 87
- 239000000203 mixture Substances 0.000 description 76
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 74
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 71
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 62
- 239000002904 solvent Substances 0.000 description 61
- 238000001914 filtration Methods 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 239000000047 product Substances 0.000 description 53
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 52
- 239000012267 brine Substances 0.000 description 51
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 51
- 239000011541 reaction mixture Substances 0.000 description 50
- 239000000741 silica gel Substances 0.000 description 49
- 229910002027 silica gel Inorganic materials 0.000 description 49
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000002244 precipitate Substances 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000000843 powder Substances 0.000 description 40
- 239000012043 crude product Substances 0.000 description 39
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 36
- 235000019341 magnesium sulphate Nutrition 0.000 description 36
- 238000007796 conventional method Methods 0.000 description 35
- 239000010410 layer Substances 0.000 description 35
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 238000007429 general method Methods 0.000 description 32
- 238000004440 column chromatography Methods 0.000 description 31
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 30
- 239000000908 ammonium hydroxide Substances 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
- 239000000463 material Substances 0.000 description 27
- 239000012044 organic layer Substances 0.000 description 27
- 230000004048 modification Effects 0.000 description 26
- 238000012986 modification Methods 0.000 description 26
- 239000013078 crystal Substances 0.000 description 25
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- 239000000706 filtrate Substances 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 21
- 238000000746 purification Methods 0.000 description 20
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 229910052717 sulfur Inorganic materials 0.000 description 19
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 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 15
- 238000010828 elution Methods 0.000 description 15
- 239000012948 isocyanate Substances 0.000 description 14
- 150000002513 isocyanates Chemical class 0.000 description 14
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 14
- 229910000029 sodium carbonate Inorganic materials 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- IQYPSFAWXDKDBA-UHFFFAOYSA-N 1,3-dihydroimidazo[4,5-c]quinolin-2-one Chemical compound C1=CC=CC2=C(NC(=O)N3)C3=CN=C21 IQYPSFAWXDKDBA-UHFFFAOYSA-N 0.000 description 13
- 238000007792 addition Methods 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 238000003818 flash chromatography Methods 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000010189 synthetic method Methods 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 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 9
- BCIBQFLFQODTNU-UHFFFAOYSA-N 7-(3-aminopropoxy)-1-(2-methylpropyl)-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=C(OCCCN)C=CC2=C(N(C(CCC)=N3)CC(C)C)C3=C(N)N=C21 BCIBQFLFQODTNU-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 9
- 229910000024 caesium carbonate Inorganic materials 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 230000028993 immune response Effects 0.000 description 9
- 238000002953 preparative HPLC Methods 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 125000003396 thiol group Chemical class [H]S* 0.000 description 9
- 239000003039 volatile agent Substances 0.000 description 9
- 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 8
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 8
- 150000001204 N-oxides Chemical class 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 8
- 102100040247 Tumor necrosis factor Human genes 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
- XTAVMVXAGPRMKN-UHFFFAOYSA-N 1-phenylmethoxyimidazo[4,5-c]quinoline Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1OCC1=CC=CC=C1 XTAVMVXAGPRMKN-UHFFFAOYSA-N 0.000 description 7
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000012065 filter cake Substances 0.000 description 7
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- GTQWQNXDDRCXMZ-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-propylimidazo[4,5-c]quinolin-7-ol Chemical compound C1=C(O)C=CC2=C3N(CCC)C(CCOC)=NC3=CN=C21 GTQWQNXDDRCXMZ-UHFFFAOYSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- IGPFOKFDBICQMC-UHFFFAOYSA-N 3-phenylmethoxyaniline Chemical compound NC1=CC=CC(OCC=2C=CC=CC=2)=C1 IGPFOKFDBICQMC-UHFFFAOYSA-N 0.000 description 6
- FIIDVVUUWRJXLF-UHFFFAOYSA-N 4-phenylmethoxyaniline Chemical compound C1=CC(N)=CC=C1OCC1=CC=CC=C1 FIIDVVUUWRJXLF-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000001805 chlorine compounds Chemical class 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 230000002452 interceptive effect Effects 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 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 5
- KZWBSKFVJCGHML-UHFFFAOYSA-N 1-(2-methylpropyl)-2-propylimidazo[4,5-c]quinolin-7-ol Chemical compound C1=C(O)C=CC2=C(N(C(CCC)=N3)CC(C)C)C3=CN=C21 KZWBSKFVJCGHML-UHFFFAOYSA-N 0.000 description 5
- GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 5
- ORCHFOSVWDGCSH-UHFFFAOYSA-N 2-butyl-1-methyl-8-(2-piperidin-4-ylethoxy)imidazo[4,5-c]quinolin-4-amine Chemical compound C=1C2=C3N(C)C(CCCC)=NC3=C(N)N=C2C=CC=1OCCC1CCNCC1 ORCHFOSVWDGCSH-UHFFFAOYSA-N 0.000 description 5
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- XYXKKZXZRUHEJG-UHFFFAOYSA-N tert-butyl N-[2-[4-amino-2-(ethoxymethyl)-1-propylimidazo[4,5-c]quinolin-7-yl]oxyethyl]carbamate Chemical compound CCCn1c(COCC)nc2c(N)nc3cc(OCCNC(=O)OC(C)(C)C)ccc3c12 XYXKKZXZRUHEJG-UHFFFAOYSA-N 0.000 description 1
- GPTXCAZYUMDUMN-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCO GPTXCAZYUMDUMN-UHFFFAOYSA-N 0.000 description 1
- ZFQWJXFJJZUVPI-UHFFFAOYSA-N tert-butyl n-(4-aminobutyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCN ZFQWJXFJJZUVPI-UHFFFAOYSA-N 0.000 description 1
- BVNVTFHJBMBITK-UHFFFAOYSA-N tert-butyl n-[2-[2-(ethoxymethyl)-5-oxido-1-propylimidazo[4,5-c]quinolin-5-ium-8-yl]oxyethyl]carbamate Chemical compound C1=CC(OCCNC(=O)OC(C)(C)C)=CC2=C3N(CCC)C(COCC)=NC3=C[N+]([O-])=C21 BVNVTFHJBMBITK-UHFFFAOYSA-N 0.000 description 1
- FGVMZOYNYSUKOU-UHFFFAOYSA-N tert-butyl n-[2-[2-methyl-1-(2-methylpropyl)imidazo[4,5-c]quinolin-7-yl]oxyethyl]carbamate Chemical compound C1=C(OCCNC(=O)OC(C)(C)C)C=CC2=C3N(CC(C)C)C(C)=NC3=CN=C21 FGVMZOYNYSUKOU-UHFFFAOYSA-N 0.000 description 1
- JHNHLZNFPLFLCS-UHFFFAOYSA-N tert-butyl n-[2-[4-amino-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)imidazo[4,5-c]quinolin-7-yl]oxyethyl]carbamate Chemical compound CCOCC1=NC2=C(N)N=C3C=C(OCCNC(=O)OC(C)(C)C)C=CC3=C2N1CC1COC(C)(C)O1 JHNHLZNFPLFLCS-UHFFFAOYSA-N 0.000 description 1
- DLJSZNKBBQMNFP-UHFFFAOYSA-N tert-butyl n-[2-[4-amino-2-methyl-1-(2-methylpropyl)imidazo[4,5-c]quinolin-7-yl]oxyethyl]carbamate Chemical compound C1=C(OCCNC(=O)OC(C)(C)C)C=CC2=C3N(CC(C)C)C(C)=NC3=C(N)N=C21 DLJSZNKBBQMNFP-UHFFFAOYSA-N 0.000 description 1
- NTHWNDWFNZFSDA-UHFFFAOYSA-N tert-butyl n-[3-[1-(2-methylpropyl)-2-propylimidazo[4,5-c]quinolin-7-yl]oxypropyl]carbamate Chemical compound C1=C(OCCCNC(=O)OC(C)(C)C)C=CC2=C(N(C(CCC)=N3)CC(C)C)C3=CN=C21 NTHWNDWFNZFSDA-UHFFFAOYSA-N 0.000 description 1
- SZMNBPZIWZLDNI-UHFFFAOYSA-N tert-butyl n-[6-[1-(2-acetamido-2-methylpropyl)-4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-7-yl]oxyhexyl]carbamate Chemical compound C1=C(OCCCCCCNC(=O)OC(C)(C)C)C=CC2=C(N(C(COCC)=N3)CC(C)(C)NC(C)=O)C3=C(N)N=C21 SZMNBPZIWZLDNI-UHFFFAOYSA-N 0.000 description 1
- CFSOIGVOPBCZOF-UHFFFAOYSA-N tert-butyl n-[6-[2-(ethoxymethyl)-1-[2-methyl-2-(propan-2-ylcarbamoylamino)propyl]-5-oxidoimidazo[4,5-c]quinolin-5-ium-7-yl]oxyhexyl]carbamate Chemical compound C1=C(OCCCCCCNC(=O)OC(C)(C)C)C=CC2=C(N(C(COCC)=N3)CC(C)(C)NC(=O)NC(C)C)C3=C[N+]([O-])=C21 CFSOIGVOPBCZOF-UHFFFAOYSA-N 0.000 description 1
- QOEHNUCGQCIQQO-UHFFFAOYSA-N tert-butyl n-[6-[2-(ethoxymethyl)-1-[2-methyl-2-(propan-2-ylcarbamoylamino)propyl]imidazo[4,5-c]quinolin-7-yl]oxyhexyl]carbamate Chemical compound C1=C(OCCCCCCNC(=O)OC(C)(C)C)C=CC2=C(N(C(COCC)=N3)CC(C)(C)NC(=O)NC(C)C)C3=CN=C21 QOEHNUCGQCIQQO-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000004886 thiomorpholines Chemical class 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 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
- 238000001665 trituration Methods 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
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- 241001430294 unidentified retrovirus Species 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 230000037314 wound repair Effects 0.000 description 1
Classifications
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- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- 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
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50863403P | 2003-10-03 | 2003-10-03 | |
| US60/508,634 | 2003-10-03 | ||
| PCT/US2004/032616 WO2005032484A2 (en) | 2003-10-03 | 2004-10-01 | Alkoxy substituted imidazoquinolines |
Publications (2)
| Publication Number | Publication Date |
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| AU2004278014A1 AU2004278014A1 (en) | 2005-04-14 |
| AU2004278014B2 true AU2004278014B2 (en) | 2011-04-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| AU2004278014A Ceased AU2004278014B2 (en) | 2003-10-03 | 2004-10-01 | Alkoxy substituted imidazoquinolines |
Country Status (17)
| Country | Link |
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| US (3) | US8871782B2 (OSRAM) |
| EP (1) | EP1673087B1 (OSRAM) |
| JP (1) | JP5043435B2 (OSRAM) |
| KR (1) | KR101154101B1 (OSRAM) |
| CN (1) | CN1897948A (OSRAM) |
| AR (1) | AR046046A1 (OSRAM) |
| AU (1) | AU2004278014B2 (OSRAM) |
| BR (1) | BRPI0414856A (OSRAM) |
| CA (1) | CA2540541C (OSRAM) |
| ES (1) | ES2544477T3 (OSRAM) |
| IL (1) | IL174654A0 (OSRAM) |
| MX (1) | MXPA06003705A (OSRAM) |
| NZ (1) | NZ546273A (OSRAM) |
| RU (1) | RU2412942C2 (OSRAM) |
| SG (1) | SG149828A1 (OSRAM) |
| WO (1) | WO2005032484A2 (OSRAM) |
| ZA (1) | ZA200603474B (OSRAM) |
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| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| EP1617845A4 (en) * | 2003-04-28 | 2006-09-20 | 3M Innovative Properties Co | COMPOSITIONS AND METHODS FOR INDUCING OPOID RECEPTORS |
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| US20090075980A1 (en) * | 2003-10-03 | 2009-03-19 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and Analogs Thereof |
| JP2007508305A (ja) | 2003-10-03 | 2007-04-05 | スリーエム イノベイティブ プロパティズ カンパニー | ピラゾロピリジンおよびその類似物 |
| US7544697B2 (en) * | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| BRPI0414856A (pt) | 2003-10-03 | 2006-11-21 | 3M Innovative Properties Co | imidazoquinolinas alcóxi-substituìdas |
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| WO2005048933A2 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime 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 |
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| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US20090270443A1 (en) * | 2004-09-02 | 2009-10-29 | Doris Stoermer | 1-amino imidazo-containing compounds and methods |
| ATE555786T1 (de) | 2004-09-02 | 2012-05-15 | 3M Innovative Properties Co | 1-alkoxy 1h-imidazo-ringsysteme und verfahren |
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| HUE025749T2 (en) | 2004-12-30 | 2016-04-28 | Meda Ab | Use of Imiquimod to treat skin metastases from breast cancer |
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| US9248127B2 (en) | 2005-02-04 | 2016-02-02 | 3M Innovative Properties Company | Aqueous gel formulations containing immune response modifiers |
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| KR20080083270A (ko) * | 2005-11-04 | 2008-09-17 | 콜레이 파마시티컬 그룹, 인코포레이티드 | 하이드록시 및 알콕시 치환된 1에이치 이미다조퀴놀린 및방법 |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 3M Innovative Properties Company | Immune response modifier conjugates |
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| US8329721B2 (en) * | 2006-03-15 | 2012-12-11 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1H-imidazonaphthyridines and methods |
| US20100168083A1 (en) * | 2006-03-21 | 2010-07-01 | Soren Ebdrup | Adamantane derivatives for the treatment of the metabolic syndrome |
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| US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
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| AU2004220534A1 (en) * | 2003-03-07 | 2004-09-23 | 3M Innovative Properties Company | 1-amino 1H-imidazoquinolines |
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| CA2540541A1 (en) | 2005-04-14 |
| NZ546273A (en) | 2009-05-31 |
| EP1673087B1 (en) | 2015-05-13 |
| US9856254B2 (en) | 2018-01-02 |
| AU2004278014A1 (en) | 2005-04-14 |
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| US20070060754A1 (en) | 2007-03-15 |
| US9365567B2 (en) | 2016-06-14 |
| KR20060118453A (ko) | 2006-11-23 |
| WO2005032484A2 (en) | 2005-04-14 |
| RU2412942C2 (ru) | 2011-02-27 |
| AR046046A1 (es) | 2005-11-23 |
| CA2540541C (en) | 2012-03-27 |
| JP5043435B2 (ja) | 2012-10-10 |
| US20160280707A1 (en) | 2016-09-29 |
| US8871782B2 (en) | 2014-10-28 |
| ZA200603474B (en) | 2008-05-28 |
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| EP1673087A4 (en) | 2009-04-08 |
| KR101154101B1 (ko) | 2012-06-11 |
| JP2007507542A (ja) | 2007-03-29 |
| CN1897948A (zh) | 2007-01-17 |
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