NO329000B1 - Tioetersubstituerte imidazokinoliner - Google Patents
Tioetersubstituerte imidazokinoliner Download PDFInfo
- Publication number
- NO329000B1 NO329000B1 NO20042356A NO20042356A NO329000B1 NO 329000 B1 NO329000 B1 NO 329000B1 NO 20042356 A NO20042356 A NO 20042356A NO 20042356 A NO20042356 A NO 20042356A NO 329000 B1 NO329000 B1 NO 329000B1
- Authority
- NO
- Norway
- Prior art keywords
- imidazo
- amine
- quinolin
- butyl
- mmol
- Prior art date
Links
- 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
- 150000001875 compounds Chemical class 0.000 claims description 117
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 75
- -1 3,5-dichlorophenyl Chemical group 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- GTNLTILAAFTUJV-UHFFFAOYSA-N 2-ethyl-1-(4-methylsulfanylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCSC)C3=C(N)N=C21 GTNLTILAAFTUJV-UHFFFAOYSA-N 0.000 claims description 5
- UDLNCSHMAKTLDW-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfonylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCCCS(C)(=O)=O)C3=C(N)N=C21 UDLNCSHMAKTLDW-UHFFFAOYSA-N 0.000 claims description 5
- RCPCTFMXMSWUKS-UHFFFAOYSA-N 1-[5-(benzenesulfonyl)pentyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCCS(=O)(=O)C1=CC=CC=C1 RCPCTFMXMSWUKS-UHFFFAOYSA-N 0.000 claims description 4
- ZUYNSIGOUBBSDP-UHFFFAOYSA-N 2-butyl-1-[4-(2,4-difluorophenyl)sulfonylbutyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCS(=O)(=O)C1=CC=C(F)C=C1F ZUYNSIGOUBBSDP-UHFFFAOYSA-N 0.000 claims description 4
- WVMAYQFQAVRDFR-UHFFFAOYSA-N 2-methyl-1-(6-methylsulfonylhexyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCCCCCS(C)(=O)=O)C3=C(N)N=C21 WVMAYQFQAVRDFR-UHFFFAOYSA-N 0.000 claims description 4
- PSILRLJUONBLBA-UHFFFAOYSA-N 1-(5-methylsulfonylpentyl)-2-(trifluoromethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCCS(=O)(=O)C)C(C(F)(F)F)=NC3=C(N)N=C21 PSILRLJUONBLBA-UHFFFAOYSA-N 0.000 claims description 3
- GCXXQFRSPDLHMH-UHFFFAOYSA-N 1-[5-(benzenesulfonyl)pentyl]-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCCS(=O)(=O)C1=CC=CC=C1 GCXXQFRSPDLHMH-UHFFFAOYSA-N 0.000 claims description 3
- YWRXEXNOWLJHGK-UHFFFAOYSA-N 2-ethyl-1-(3-methylsulfanylpropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCSC)C3=C(N)N=C21 YWRXEXNOWLJHGK-UHFFFAOYSA-N 0.000 claims description 3
- YTKBNHFEQWYUAH-UHFFFAOYSA-N 2-ethyl-1-(4-pyrimidin-2-ylsulfonylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound CCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCS(=O)(=O)C1=NC=CC=N1 YTKBNHFEQWYUAH-UHFFFAOYSA-N 0.000 claims description 3
- ABGVXOMZHFFGNE-UHFFFAOYSA-N 2-methyl-1-(3-methylsulfanylpropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCSC)C(C)=NC3=C(N)N=C21 ABGVXOMZHFFGNE-UHFFFAOYSA-N 0.000 claims description 3
- HRQAQBGWJDCOAX-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfinylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCCCS(C)=O)C3=C(N)N=C21 HRQAQBGWJDCOAX-UHFFFAOYSA-N 0.000 claims description 3
- PUDPBYLGLQKPCE-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfonylbutyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(C)=N3)CCCCS(C)(=O)=O)C3=C(N)N=C21 PUDPBYLGLQKPCE-UHFFFAOYSA-N 0.000 claims description 3
- UFHWCELTQCMDMH-UHFFFAOYSA-N 1-(2-methylsulfonylethyl)-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCS(C)(=O)=O)C3=C(N)N=C21 UFHWCELTQCMDMH-UHFFFAOYSA-N 0.000 claims description 2
- OEHZFBFYCHNCLU-UHFFFAOYSA-N 1-(4-butylsulfanylbutyl)-2-ethylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCSCCCC)C(CC)=NC3=C(N)N=C21 OEHZFBFYCHNCLU-UHFFFAOYSA-N 0.000 claims description 2
- SMRXSSOYHRBMFG-UHFFFAOYSA-N 1-(4-methylsulfonylbutyl)-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCS(C)(=O)=O)C3=C(N)N=C21 SMRXSSOYHRBMFG-UHFFFAOYSA-N 0.000 claims description 2
- GHDIDOLENUUOGS-UHFFFAOYSA-N 1-(5-methylsulfonylpentyl)-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCCS(C)(=O)=O)C3=C(N)N=C21 GHDIDOLENUUOGS-UHFFFAOYSA-N 0.000 claims description 2
- RLGNIXAVMDVPSM-UHFFFAOYSA-N 1-[4-(3,5-dichlorophenyl)sulfonylbutyl]-2-ethylimidazo[4,5-c]quinolin-4-amine Chemical compound CCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 RLGNIXAVMDVPSM-UHFFFAOYSA-N 0.000 claims description 2
- FDPITCVMTYQHSL-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)sulfanylbutyl]-2-ethylimidazo[4,5-c]quinolin-4-amine Chemical compound CCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCSC1=CC=C(Cl)C=C1 FDPITCVMTYQHSL-UHFFFAOYSA-N 0.000 claims description 2
- IARQILIVTJNBRO-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)sulfonylbutyl]-2-methyl-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound CC1=NC2=C(N)N=C3CCCCC3=C2N1CCCCS(=O)(=O)C1=CC=C(F)C=C1 IARQILIVTJNBRO-UHFFFAOYSA-N 0.000 claims description 2
- ICNADGWYNDEDGA-UHFFFAOYSA-N 2-butyl-1-(2-ethylsulfanylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCSCC)C3=C(N)N=C21 ICNADGWYNDEDGA-UHFFFAOYSA-N 0.000 claims description 2
- PDIQZHBHPOJOCI-UHFFFAOYSA-N 2-butyl-1-(2-methylsulfonylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCS(C)(=O)=O)C3=C(N)N=C21 PDIQZHBHPOJOCI-UHFFFAOYSA-N 0.000 claims description 2
- XIJRZMMUTWXAOG-UHFFFAOYSA-N 2-butyl-1-[4-(2,4-difluorophenyl)sulfanylbutyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCSC1=CC=C(F)C=C1F XIJRZMMUTWXAOG-UHFFFAOYSA-N 0.000 claims description 2
- VLYQYLBDPVDVTK-UHFFFAOYSA-N 2-butyl-1-[4-(4-fluorophenyl)sulfonylbutyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCS(=O)(=O)C1=CC=C(F)C=C1 VLYQYLBDPVDVTK-UHFFFAOYSA-N 0.000 claims description 2
- YHNHAZQRVHGKLO-UHFFFAOYSA-N 2-ethyl-1-(2-methylsulfonylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCS(C)(=O)=O)C3=C(N)N=C21 YHNHAZQRVHGKLO-UHFFFAOYSA-N 0.000 claims description 2
- PGJVGBQPYLZUBU-UHFFFAOYSA-N 2-ethyl-1-(3-methylsulfonylpropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCS(C)(=O)=O)C3=C(N)N=C21 PGJVGBQPYLZUBU-UHFFFAOYSA-N 0.000 claims description 2
- RLRCLBKPDAODDG-UHFFFAOYSA-N 2-ethyl-1-(4-ethylsulfonylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCS(=O)(=O)CC)C3=C(N)N=C21 RLRCLBKPDAODDG-UHFFFAOYSA-N 0.000 claims description 2
- UNHHOPAROWIFAN-UHFFFAOYSA-N 2-ethyl-1-(4-methylsulfonylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCS(C)(=O)=O)C3=C(N)N=C21 UNHHOPAROWIFAN-UHFFFAOYSA-N 0.000 claims description 2
- UQVOYBQMGUYKBJ-UHFFFAOYSA-N 2-methyl-1-(2-methylsulfanylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCSC)C(C)=NC3=C(N)N=C21 UQVOYBQMGUYKBJ-UHFFFAOYSA-N 0.000 claims description 2
- ZOOSAKFXYOBUCR-UHFFFAOYSA-N 2-methyl-1-(2-methylsulfonylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCS(C)(=O)=O)C3=C(N)N=C21 ZOOSAKFXYOBUCR-UHFFFAOYSA-N 0.000 claims description 2
- ZIDMRFPPPAEFNZ-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCSC)C(C)=NC3=C(N)N=C21 ZIDMRFPPPAEFNZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- KNIOKHOHPNEDFO-UHFFFAOYSA-N 1-(4-butylsulfonylbutyl)-2-ethylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCS(=O)(=O)CCCC)C(CC)=NC3=C(N)N=C21 KNIOKHOHPNEDFO-UHFFFAOYSA-N 0.000 claims 1
- UYIJGKDDBFJNIE-UHFFFAOYSA-N 1-(4-cyclohexylsulfonylbutyl)-2-ethylimidazo[4,5-c]quinolin-4-amine Chemical compound CCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCS(=O)(=O)C1CCCCC1 UYIJGKDDBFJNIE-UHFFFAOYSA-N 0.000 claims 1
- VRTQRXJGLVQIPR-UHFFFAOYSA-N 1-(4-tert-butylsulfonylbutyl)-2-methyl-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(C)=N3)CCCCS(=O)(=O)C(C)(C)C)C3=C(N)N=C21 VRTQRXJGLVQIPR-UHFFFAOYSA-N 0.000 claims 1
- UOGSEZIEPYRILA-UHFFFAOYSA-N 1-[2-(benzenesulfonyl)ethyl]-2-butylimidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCS(=O)(=O)C1=CC=CC=C1 UOGSEZIEPYRILA-UHFFFAOYSA-N 0.000 claims 1
- JUJBVPPOMWXYSD-UHFFFAOYSA-N 2-butyl-1-(2-ethylsulfonylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCS(=O)(=O)CC)C3=C(N)N=C21 JUJBVPPOMWXYSD-UHFFFAOYSA-N 0.000 claims 1
- YQUGGLAFTLRIOP-UHFFFAOYSA-N 2-butyl-1-(2-propylsulfonylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCS(=O)(=O)CCC)C3=C(N)N=C21 YQUGGLAFTLRIOP-UHFFFAOYSA-N 0.000 claims 1
- YKXPDKKWHNPUED-UHFFFAOYSA-N 2-butyl-1-(2-tert-butylsulfanylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCSC(C)(C)C)C3=C(N)N=C21 YKXPDKKWHNPUED-UHFFFAOYSA-N 0.000 claims 1
- WPJQSOSNXMXNIA-UHFFFAOYSA-N 2-butyl-1-(2-tert-butylsulfonylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCS(=O)(=O)C(C)(C)C)C3=C(N)N=C21 WPJQSOSNXMXNIA-UHFFFAOYSA-N 0.000 claims 1
- GKPDLXUCSGJQIN-UHFFFAOYSA-N 2-butyl-1-[2-(2-methylpropylsulfanyl)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCSCC(C)C)C3=C(N)N=C21 GKPDLXUCSGJQIN-UHFFFAOYSA-N 0.000 claims 1
- MSGQPABFZUHUGE-UHFFFAOYSA-N 2-butyl-1-[4-(4-fluorophenyl)sulfanylbutyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCSC1=CC=C(F)C=C1 MSGQPABFZUHUGE-UHFFFAOYSA-N 0.000 claims 1
- YQKJWZHRAKCVKC-UHFFFAOYSA-N 2-ethyl-1-(4-propan-2-ylsulfanylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCSC(C)C)C3=C(N)N=C21 YQKJWZHRAKCVKC-UHFFFAOYSA-N 0.000 claims 1
- FIDUHWIPSJSYCN-UHFFFAOYSA-N 2-ethyl-1-(4-propan-2-ylsulfonylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCS(=O)(=O)C(C)C)C3=C(N)N=C21 FIDUHWIPSJSYCN-UHFFFAOYSA-N 0.000 claims 1
- XDLBJJMSISUHJR-UHFFFAOYSA-N 2-ethyl-1-[4-(4-fluorophenyl)sulfanylbutyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCSC1=CC=C(F)C=C1 XDLBJJMSISUHJR-UHFFFAOYSA-N 0.000 claims 1
- XWZZHWXWYZLKPT-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfonylpentyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C3N(CCCC(C)S(C)(=O)=O)C(C)=NC3=C(N)N=C21 XWZZHWXWYZLKPT-UHFFFAOYSA-N 0.000 claims 1
- YJTOZVGZEOGNTN-UHFFFAOYSA-N 2-methyl-1-(4-propan-2-ylsulfonylbutyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C3N(CCCCS(=O)(=O)C(C)C)C(C)=NC3=C(N)N=C21 YJTOZVGZEOGNTN-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 198
- 239000007787 solid Substances 0.000 description 158
- 238000000034 method Methods 0.000 description 137
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 126
- 229910052799 carbon Inorganic materials 0.000 description 124
- 229910052739 hydrogen Inorganic materials 0.000 description 122
- 229910052757 nitrogen Inorganic materials 0.000 description 115
- 238000006243 chemical reaction Methods 0.000 description 109
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- 239000000243 solution Substances 0.000 description 101
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 77
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- 238000004458 analytical method Methods 0.000 description 58
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 57
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 39
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
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- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 18
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- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 17
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US10/013,059 US6664264B2 (en) | 2000-12-08 | 2001-12-06 | Thioether substituted imidazoquinolines |
PCT/US2002/018290 WO2003050121A1 (en) | 2001-12-06 | 2002-06-07 | Thioether substituted imidazoquinolines |
Publications (2)
Publication Number | Publication Date |
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NO20042356L NO20042356L (no) | 2004-08-12 |
NO329000B1 true NO329000B1 (no) | 2010-07-19 |
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NO20042356A NO329000B1 (no) | 2001-12-06 | 2004-06-07 | Tioetersubstituerte imidazokinoliner |
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US (3) | US6664264B2 (es) |
EP (1) | EP1451191A1 (es) |
JP (2) | JP2005511747A (es) |
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WO (1) | WO2003050121A1 (es) |
ZA (1) | ZA200405338B (es) |
Families Citing this family (176)
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US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
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 |
US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
JP3436512B2 (ja) * | 1999-12-28 | 2003-08-11 | 株式会社デンソー | アクセル装置 |
US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
US6677348B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
US6677347B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
US6545017B1 (en) * | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
UA75622C2 (en) * | 2000-12-08 | 2006-05-15 | 3M Innovative Properties Co | Aryl ether substituted imidazoquinolines, pharmaceutical composition based thereon |
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 |
US6664265B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
US7226928B2 (en) * | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
US7321033B2 (en) * | 2001-11-27 | 2008-01-22 | Anadys Pharmaceuticals, Inc. | 3-B-D-ribofuranosylthiazolo [4,5-d] pyrimidine nucleosides and uses thereof |
US6677349B1 (en) * | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
US7030129B2 (en) | 2002-02-22 | 2006-04-18 | 3M Innovative Properties Company | Method of reducing and treating UVB-induced immunosuppression |
BR0311648A (pt) * | 2002-06-07 | 2005-04-19 | 3M Innovative Properties Co | Imidazopiridinas substituìdas por éter |
WO2004058759A1 (en) | 2002-12-20 | 2004-07-15 | 3M Innovative Properties Company | Aryl / hetaryl substituted imidazoquinolines |
EP2572714A1 (en) | 2002-12-30 | 2013-03-27 | 3M Innovative Properties Company | Immunostimulatory Combinations |
JP2006517974A (ja) * | 2003-02-13 | 2006-08-03 | スリーエム イノベイティブ プロパティズ カンパニー | Irm化合物およびトル様受容体8に関する方法および組成物 |
EP1599726A4 (en) * | 2003-02-27 | 2009-07-22 | 3M Innovative Properties Co | SELECTIVE MODULATION OF TLR-MEDIATED BIOLOGICAL ACTIVITY |
CA2517528A1 (en) | 2003-03-04 | 2004-09-16 | 3M Innovative Properties Company | Prophylactic treatment of uv-induced epidermal neoplasia |
MXPA05009488A (es) * | 2003-03-07 | 2005-12-14 | 3M Innovative Properties Co | 1-amino 1h-imidazoquinolinas. |
US7163947B2 (en) * | 2003-03-07 | 2007-01-16 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
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CN1599741A (zh) | 2005-03-23 |
NZ533038A (en) | 2005-12-23 |
WO2003050121A1 (en) | 2003-06-19 |
JP5319477B2 (ja) | 2013-10-16 |
MXPA04005362A (es) | 2004-09-27 |
JP2010031024A (ja) | 2010-02-12 |
RU2004117160A (ru) | 2006-01-10 |
CA2468517A1 (en) | 2003-06-19 |
JP2005511747A (ja) | 2005-04-28 |
KR20040105692A (ko) | 2004-12-16 |
US6664264B2 (en) | 2003-12-16 |
US20050209267A1 (en) | 2005-09-22 |
HRP20040505A2 (en) | 2004-12-31 |
EP1451191A1 (en) | 2004-09-01 |
CN1235900C (zh) | 2006-01-11 |
AU2002315009A1 (en) | 2003-06-23 |
US7288550B2 (en) | 2007-10-30 |
NO20042356L (no) | 2004-08-12 |
PL370661A1 (en) | 2005-05-30 |
ZA200405338B (en) | 2005-07-12 |
IL162054A0 (en) | 2005-11-20 |
US20020173655A1 (en) | 2002-11-21 |
CA2468517C (en) | 2011-01-04 |
BR0214750A (pt) | 2004-09-14 |
US20040102471A1 (en) | 2004-05-27 |
RU2304143C2 (ru) | 2007-08-10 |
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