HRP20040505A2 - Thioether substituted imidazoquinolines - Google Patents
Thioether substituted imidazoquinolinesInfo
- Publication number
- HRP20040505A2 HRP20040505A2 HRP20040505A HRP20040505A2 HR P20040505 A2 HRP20040505 A2 HR P20040505A2 HR P20040505 A HRP20040505 A HR P20040505A HR P20040505 A2 HRP20040505 A2 HR P20040505A2
- Authority
- HR
- Croatia
- 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 2
- 125000000101 thioether group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 122
- -1 1-[4-(cyclohexylisopropyl)butyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine Chemical compound 0.000 claims description 60
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 16
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 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 7
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
- 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 5
- BKGNMAXFNRGTTI-UHFFFAOYSA-N 2-ethyl-1-(4-pyrimidin-2-ylsulfanylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound CCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCSC1=NC=CC=N1 BKGNMAXFNRGTTI-UHFFFAOYSA-N 0.000 claims description 5
- WCQSIYIMJKOHHD-UHFFFAOYSA-N 2-methyl-1-(3-methylsulfonylpropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCCS(C)(=O)=O)C3=C(N)N=C21 WCQSIYIMJKOHHD-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 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 4
- 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 4
- 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
- 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 4
- FZFFOPUDCBKJRW-UHFFFAOYSA-N 2-butyl-1-(4-methylsulfinylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCS(C)=O)C3=C(N)N=C21 FZFFOPUDCBKJRW-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
- 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 4
- 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 4
- 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 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 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 3
- 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
- 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 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
- 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 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
- 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 3
- 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 3
- 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
- OGOLCWLIKAUPJH-UHFFFAOYSA-N 1-(4-cyclopentylsulfonylbutyl)-2-ethylimidazo[4,5-c]quinolin-4-amine Chemical compound CCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCS(=O)(=O)C1CCCC1 OGOLCWLIKAUPJH-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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 description 2
- 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 description 2
- AXEGVBWOAYSSGT-UHFFFAOYSA-N 2-butyl-1-(4-ethylsulfonylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCS(=O)(=O)CC)C3=C(N)N=C21 AXEGVBWOAYSSGT-UHFFFAOYSA-N 0.000 claims description 2
- CPDRIEPFQSJYTJ-UHFFFAOYSA-N 2-butyl-1-[2-(4-fluorophenyl)sulfonylethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCS(=O)(=O)C1=CC=C(F)C=C1 CPDRIEPFQSJYTJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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
- LSCSFWLZNXGBDK-UHFFFAOYSA-N 2-ethyl-1-(4-ethylsulfanylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCSCC)C(CC)=NC3=C(N)N=C21 LSCSFWLZNXGBDK-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
- 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
- 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 2
- 239000003937 drug carrier Substances 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
- DLHBGVVCZWLGFR-UHFFFAOYSA-N 1-(4-cyclohexylsulfanylbutyl)-2-ethylimidazo[4,5-c]quinolin-4-amine Chemical compound CCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCSC1CCCCC1 DLHBGVVCZWLGFR-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
- SIHCMNJJWTWOSY-UHFFFAOYSA-N 1-[4-(3,5-dichlorophenyl)sulfanylbutyl]-2-ethylimidazo[4,5-c]quinolin-4-amine Chemical compound CCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCSC1=CC(Cl)=CC(Cl)=C1 SIHCMNJJWTWOSY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QNOFMVQFCHBXPU-UHFFFAOYSA-N 2-butyl-1-(2-propan-2-ylsulfonylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCS(=O)(=O)C(C)C)C3=C(N)N=C21 QNOFMVQFCHBXPU-UHFFFAOYSA-N 0.000 claims 1
- ORLOWKBQFORZPQ-UHFFFAOYSA-N 2-butyl-1-(2-propylsulfanylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCSCCC)C3=C(N)N=C21 ORLOWKBQFORZPQ-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
- 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
- WJZZAWGYEFFFES-UHFFFAOYSA-N 2-butyl-1-(4-tert-butylsulfanylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCSC(C)(C)C)C3=C(N)N=C21 WJZZAWGYEFFFES-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
- IKXYWGDGQRWBDB-UHFFFAOYSA-N 2-butyl-1-[2-(2-methylpropylsulfonyl)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCS(=O)(=O)CC(C)C)C3=C(N)N=C21 IKXYWGDGQRWBDB-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 207
- 239000007787 solid Substances 0.000 description 154
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- 238000006243 chemical reaction Methods 0.000 description 135
- 239000000243 solution Substances 0.000 description 130
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 124
- 229910052739 hydrogen Inorganic materials 0.000 description 117
- 229910052799 carbon Inorganic materials 0.000 description 115
- 229910052757 nitrogen Inorganic materials 0.000 description 112
- 238000007429 general method Methods 0.000 description 108
- 239000000463 material Substances 0.000 description 95
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 74
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
- 238000004458 analytical method Methods 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 54
- 239000011541 reaction mixture Substances 0.000 description 51
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 50
- 239000010410 layer Substances 0.000 description 45
- 239000003921 oil Substances 0.000 description 45
- 235000019198 oils Nutrition 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 238000002844 melting Methods 0.000 description 42
- 230000008018 melting Effects 0.000 description 42
- 238000000746 purification Methods 0.000 description 42
- 239000012044 organic layer Substances 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 229920006395 saturated elastomer Polymers 0.000 description 39
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 38
- 238000003756 stirring Methods 0.000 description 37
- 239000000047 product Substances 0.000 description 36
- 238000001914 filtration Methods 0.000 description 34
- 239000000843 powder Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- 239000000741 silica gel Substances 0.000 description 32
- 229910002027 silica gel Inorganic materials 0.000 description 32
- 235000017557 sodium bicarbonate Nutrition 0.000 description 32
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 32
- 238000000034 method Methods 0.000 description 31
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 (1)
Publication Number | Publication Date |
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HRP20040505A2 true HRP20040505A2 (en) | 2004-12-31 |
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Application Number | Title | Priority Date | Filing Date |
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HRP20040505 HRP20040505A2 (en) | 2001-12-06 | 2004-06-04 | Thioether substituted imidazoquinolines |
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US (3) | US6664264B2 (ja) |
EP (1) | EP1451191A1 (ja) |
JP (2) | JP2005511747A (ja) |
KR (1) | KR20040105692A (ja) |
CN (1) | CN1235900C (ja) |
BR (1) | BR0214750A (ja) |
CA (1) | CA2468517C (ja) |
HR (1) | HRP20040505A2 (ja) |
IL (1) | IL162054A0 (ja) |
MX (1) | MXPA04005362A (ja) |
NO (1) | NO329000B1 (ja) |
NZ (1) | NZ533038A (ja) |
PL (1) | PL370661A1 (ja) |
RU (1) | RU2304143C2 (ja) |
WO (1) | WO2003050121A1 (ja) |
ZA (1) | ZA200405338B (ja) |
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WO2004071459A2 (en) | 2003-02-13 | 2004-08-26 | 3M Innovative Properties Company | Methods and compositions related to irm compounds and toll-like receptor 8 |
JP2006519020A (ja) | 2003-02-27 | 2006-08-24 | スリーエム イノベイティブ プロパティズ カンパニー | Tlr介在生物活性の選択的調節 |
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KR20050107497A (ko) | 2003-03-07 | 2005-11-11 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 1-아미노 1h-이미다조퀴놀린 |
EP1603476A4 (en) | 2003-03-13 | 2010-01-13 | 3M Innovative Properties Co | PROCESS FOR REMOVING TATTOO |
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US20040191833A1 (en) | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Selective activation of cellular activities mediated through a common toll-like receptor |
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ATE465742T1 (de) | 2003-09-05 | 2010-05-15 | Anadys Pharmaceuticals Inc | Tlr7-liganden zur behandlung von hepatitis c |
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Also Published As
Publication number | Publication date |
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CN1235900C (zh) | 2006-01-11 |
JP2005511747A (ja) | 2005-04-28 |
US6921826B2 (en) | 2005-07-26 |
US7288550B2 (en) | 2007-10-30 |
JP5319477B2 (ja) | 2013-10-16 |
US20020173655A1 (en) | 2002-11-21 |
RU2004117160A (ru) | 2006-01-10 |
JP2010031024A (ja) | 2010-02-12 |
PL370661A1 (en) | 2005-05-30 |
RU2304143C2 (ru) | 2007-08-10 |
WO2003050121A1 (en) | 2003-06-19 |
KR20040105692A (ko) | 2004-12-16 |
BR0214750A (pt) | 2004-09-14 |
ZA200405338B (en) | 2005-07-12 |
CA2468517C (en) | 2011-01-04 |
EP1451191A1 (en) | 2004-09-01 |
US20050209267A1 (en) | 2005-09-22 |
MXPA04005362A (es) | 2004-09-27 |
US20040102471A1 (en) | 2004-05-27 |
AU2002315009A1 (en) | 2003-06-23 |
NO20042356L (no) | 2004-08-12 |
CA2468517A1 (en) | 2003-06-19 |
NO329000B1 (no) | 2010-07-19 |
IL162054A0 (en) | 2005-11-20 |
NZ533038A (en) | 2005-12-23 |
US6664264B2 (en) | 2003-12-16 |
CN1599741A (zh) | 2005-03-23 |
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