NO316564B1 - Fremgangsmåte til fremstilling av imidazokinolinaminer - Google Patents
Fremgangsmåte til fremstilling av imidazokinolinaminer Download PDFInfo
- Publication number
- NO316564B1 NO316564B1 NO986002A NO986002A NO316564B1 NO 316564 B1 NO316564 B1 NO 316564B1 NO 986002 A NO986002 A NO 986002A NO 986002 A NO986002 A NO 986002A NO 316564 B1 NO316564 B1 NO 316564B1
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- alkyl
- substituted
- phenyl
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title description 6
- WSIZDLIFQIDDKA-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinolin-2-amine Chemical class C1=CC=NC2=C(NC(N)=N3)C3=CC=C21 WSIZDLIFQIDDKA-UHFFFAOYSA-N 0.000 title 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 210
- 125000000217 alkyl group Chemical group 0.000 claims description 107
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- -1 (phenyl)ethyl Chemical group 0.000 claims description 45
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 37
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 150000003536 tetrazoles Chemical class 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- GYESAYHWISMZOK-UHFFFAOYSA-N quinolin-5-ol Chemical compound C1=CC=C2C(O)=CC=CC2=N1 GYESAYHWISMZOK-UHFFFAOYSA-N 0.000 claims description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 claims description 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- NYDAOEQPKZSNOI-UHFFFAOYSA-N quinoline-4,5-diamine Chemical compound C1=CC(N)=C2C(N)=CC=CC2=N1 NYDAOEQPKZSNOI-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- XMIAFAKRAAMSGX-UHFFFAOYSA-N quinolin-5-amine Chemical compound C1=CC=C2C(N)=CC=CC2=N1 XMIAFAKRAAMSGX-UHFFFAOYSA-N 0.000 claims description 7
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical group C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 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 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- BTHZSGJQDAHDGL-UHFFFAOYSA-N 2,3,4,5,8,10-hexazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(16),3,5,7(11),9,12,14-heptaene Chemical compound C12=NN=NN2C2=CC=CC=C2C2=C1N=CN2 BTHZSGJQDAHDGL-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
- 239000011541 reaction mixture Substances 0.000 description 45
- 239000007787 solid Substances 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 238000001914 filtration Methods 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000007796 conventional method Methods 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical group FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- QOIPJVLRQGAKQX-UHFFFAOYSA-N 2-(5-methyltetrazol-1-yl)benzoic acid Chemical compound CC1=NN=NN1C1=CC=CC=C1C(O)=O QOIPJVLRQGAKQX-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 150000003461 sulfonyl halides Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- CNBOKXFMODKQCT-UHFFFAOYSA-N 1-(4-aminoimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol Chemical compound C1=CC=CC2=C3N(CC(C)(O)C)C=NC3=C(N)N=C21 CNBOKXFMODKQCT-UHFFFAOYSA-N 0.000 description 2
- KCVIRDLVBXYYKD-UHFFFAOYSA-N 1-nitrotetrazole Chemical compound [O-][N+](=O)N1C=NN=N1 KCVIRDLVBXYYKD-UHFFFAOYSA-N 0.000 description 2
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 2
- WMQSKECCMQRJRX-UHFFFAOYSA-N 2-methyl-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C)=NC2=C1 WMQSKECCMQRJRX-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- IRUNKQSGDBYUDC-UHFFFAOYSA-N diethoxymethyl acetate Chemical compound CCOC(OCC)OC(C)=O IRUNKQSGDBYUDC-UHFFFAOYSA-N 0.000 description 2
- JQPAALBDXTUHTI-UHFFFAOYSA-N ethyl 2-(5-methyltetrazol-1-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1N1C(C)=NN=N1 JQPAALBDXTUHTI-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- TYEYDNVMXOUYSV-UHFFFAOYSA-N 1,4-dichloro-3-nitro-2h-quinoline Chemical compound C1=CC=C2N(Cl)CC([N+](=O)[O-])=C(Cl)C2=C1 TYEYDNVMXOUYSV-UHFFFAOYSA-N 0.000 description 1
- DHXCFDWZILVFEQ-UHFFFAOYSA-N 1-(4-chloroimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol Chemical compound C1=CC=CC2=C3N(CC(C)(O)C)C=NC3=C(Cl)N=C21 DHXCFDWZILVFEQ-UHFFFAOYSA-N 0.000 description 1
- JTQRHJOAARSHIV-UHFFFAOYSA-N 1-[(2-chloro-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol Chemical compound C1=CC=C2C(NCC(C)(O)C)=C([N+]([O-])=O)C(Cl)=NC2=C1 JTQRHJOAARSHIV-UHFFFAOYSA-N 0.000 description 1
- LXQMHOKEXZETKB-UHFFFAOYSA-N 1-amino-2-methylpropan-2-ol Chemical compound CC(C)(O)CN LXQMHOKEXZETKB-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
- SHKUAAUCZDOPDI-UHFFFAOYSA-N 4-chloro-3h-imidazo[4,5-c]quinoline Chemical compound ClC1=NC2=CC=CC=C2C2=C1N=CN2 SHKUAAUCZDOPDI-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZKMXEKRSQNHUEK-UHFFFAOYSA-N C1=CC=C2C(S(O)(=O)=O)=C([N+]([O-])=O)C(S(=O)(=O)O)=NC2=C1 Chemical compound C1=CC=C2C(S(O)(=O)=O)=C([N+]([O-])=O)C(S(=O)(=O)O)=NC2=C1 ZKMXEKRSQNHUEK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical group F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 102000015696 Interleukins Human genes 0.000 description 1
- 108010063738 Interleukins Proteins 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- GJYVZUKSNFSLCL-UHFFFAOYSA-N dichloromethanol Chemical compound OC(Cl)Cl GJYVZUKSNFSLCL-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/673,712 US5741908A (en) | 1996-06-21 | 1996-06-21 | Process for reparing imidazoquinolinamines |
| PCT/US1996/016972 WO1997048704A1 (en) | 1996-06-21 | 1996-10-22 | Process for preparing imidazoquinolinamines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO986002L NO986002L (no) | 1998-12-18 |
| NO986002D0 NO986002D0 (no) | 1998-12-18 |
| NO316564B1 true NO316564B1 (no) | 2004-02-23 |
Family
ID=24703817
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO986002A NO316564B1 (no) | 1996-06-21 | 1998-12-18 | Fremgangsmåte til fremstilling av imidazokinolinaminer |
| NO20032134A NO318095B1 (no) | 1996-06-21 | 2003-05-12 | Fremgangsmate til fremstilling av imidazokinolin-aminer |
| NO20032133A NO318213B1 (no) | 1996-06-21 | 2003-05-12 | Fremgangsmate til fremstilling av imidazokinolinaminer |
| NO20032132A NO318094B1 (no) | 1996-06-21 | 2003-05-12 | Fremgangsmate til fremstilling av imidazokinolin-aminer |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20032134A NO318095B1 (no) | 1996-06-21 | 2003-05-12 | Fremgangsmate til fremstilling av imidazokinolin-aminer |
| NO20032133A NO318213B1 (no) | 1996-06-21 | 2003-05-12 | Fremgangsmate til fremstilling av imidazokinolinaminer |
| NO20032132A NO318094B1 (no) | 1996-06-21 | 2003-05-12 | Fremgangsmate til fremstilling av imidazokinolin-aminer |
Country Status (15)
| Country | Link |
|---|---|
| US (9) | US5741908A (OSRAM) |
| EP (1) | EP0912565B1 (OSRAM) |
| JP (1) | JP4139915B2 (OSRAM) |
| KR (3) | KR20040029475A (OSRAM) |
| AT (1) | ATE264326T1 (OSRAM) |
| AU (1) | AU721036B2 (OSRAM) |
| CA (1) | CA2257846C (OSRAM) |
| DE (1) | DE69632207T2 (OSRAM) |
| DK (1) | DK0912565T3 (OSRAM) |
| ES (1) | ES2215203T3 (OSRAM) |
| IL (5) | IL148318A0 (OSRAM) |
| NO (4) | NO316564B1 (OSRAM) |
| NZ (1) | NZ333169A (OSRAM) |
| PT (1) | PT912565E (OSRAM) |
| WO (1) | WO1997048704A1 (OSRAM) |
Families Citing this family (156)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6608201B2 (en) * | 1992-08-28 | 2003-08-19 | 3M Innovative Properties Company | Process for preparing 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| 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 |
| US6518280B2 (en) | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
| US6486168B1 (en) | 1999-01-08 | 2002-11-26 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| US6245776B1 (en) | 1999-01-08 | 2001-06-12 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| US6558951B1 (en) * | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| 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 |
| US6573273B1 (en) * | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| US6916925B1 (en) | 1999-11-05 | 2005-07-12 | 3M Innovative Properties Co. | Dye labeled imidazoquinoline compounds |
| JP3436512B2 (ja) * | 1999-12-28 | 2003-08-11 | 株式会社デンソー | アクセル装置 |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| US6677348B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| US6677347B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| UA74852C2 (en) * | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
| US6664265B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6660735B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| US6660747B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| JP2008531580A (ja) * | 2000-12-08 | 2008-08-14 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答修飾因子の標的化送達のための組成物および方法 |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US7226928B2 (en) * | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
| EP1427445A4 (en) * | 2001-08-30 | 2006-09-06 | 3M Innovative Properties Co | METHODS OF MATURING PLASMOCYTOID DENDRITIC CELLS USING MOLECULES MODIFYING IMMUNE RESPONSES |
| US20040014779A1 (en) * | 2001-11-16 | 2004-01-22 | 3M Innovative Properties Company | Methods and compositions related to IRM compounds and toll-like recptor pathways |
| AU2004220469B2 (en) * | 2001-11-29 | 2010-07-29 | 3M Innovative Properties Company | Methods of improving skin quality |
| WO2003045391A1 (en) * | 2001-11-29 | 2003-06-05 | 3M Innovative Properties Company | Pharmaceutical formulations comprising an immune response modifier |
| CA2365732A1 (en) * | 2001-12-20 | 2003-06-20 | Ibm Canada Limited-Ibm Canada Limitee | Testing measurements |
| US6677349B1 (en) | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| GB0204014D0 (en) * | 2002-02-20 | 2002-04-03 | Univ Surrey | Improvements relating to multifilar helix antennas |
| WO2003072026A2 (en) * | 2002-02-22 | 2003-09-04 | 3M Innovative Properties Company | Method of reducing and treating uvb-induced immunosuppression |
| US6743920B2 (en) | 2002-05-29 | 2004-06-01 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| US6797718B2 (en) * | 2002-06-07 | 2004-09-28 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| PT1543002E (pt) | 2002-07-23 | 2006-11-30 | Teva Gyogyszergyar Zartkoeruen | Preparação de intermediários 1h-imidazo ( 4,5-c )quinolin-4-aminas via 1h- imidazo (4,5-c ) quinolina-4-ftalimida |
| HRP20050183A2 (en) | 2002-07-26 | 2005-06-30 | Teva Gy�gyszergy�r R�szv�nyt�rsas�g | Preparation of 1h-imidazo [4,5-c]quinolin-4-aminesvia novel 1h-imidazo [4,5-c]quinolin-4-cyano and 1h-imidazo [4,5-c]quinolin-4-carboxamide intermediates |
| AU2003299863B2 (en) | 2002-08-15 | 2009-09-24 | 3M Innovative Properties Company | Immunostimulatory compositions and methods of stimulating an immune response |
| JP2006503068A (ja) * | 2002-09-26 | 2006-01-26 | スリーエム イノベイティブ プロパティズ カンパニー | １ｈ−イミダゾダイマー |
| WO2004053057A2 (en) * | 2002-12-11 | 2004-06-24 | 3M Innovative Properties Company | Gene expression systems and recombinant cell lines |
| AU2003287316A1 (en) * | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Assays relating to toll-like receptor activity |
| NZ540826A (en) | 2002-12-20 | 2008-07-31 | 3M Innovative Properties Co | Aryl / hetaryl substituted imidazoquinolines |
| WO2004060319A2 (en) | 2002-12-30 | 2004-07-22 | 3M Innovative Properties Company | Immunostimulatory combinations |
| WO2004071459A2 (en) * | 2003-02-13 | 2004-08-26 | 3M Innovative Properties Company | Methods and compositions related to irm compounds and toll-like receptor 8 |
| US7485432B2 (en) * | 2003-02-27 | 2009-02-03 | 3M Innovative Properties Company | Selective modulation of TLR-mediated biological activity |
| EP1601365A4 (en) | 2003-03-04 | 2009-11-11 | 3M Innovative Properties Co | PROPHYLACTIC TREATMENT OF UV-INDUCED EPIDERMAL NEOPLASIA |
| US7163947B2 (en) * | 2003-03-07 | 2007-01-16 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
| KR20050107497A (ko) * | 2003-03-07 | 2005-11-11 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 1-아미노 1ｈ-이미다조퀴놀린 |
| WO2004080293A2 (en) * | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Methods for diagnosing skin lesions |
| AU2004220465A1 (en) * | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Method of tattoo removal |
| US20040192585A1 (en) * | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
| US20040265351A1 (en) * | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| AU2004229478B2 (en) * | 2003-04-10 | 2009-12-24 | 3M Innovative Properties Company | Delivery of immune response modifier compounds |
| US20040214851A1 (en) * | 2003-04-28 | 2004-10-28 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
| WO2004110991A2 (en) * | 2003-06-06 | 2004-12-23 | 3M Innovative Properties Company | PROCESS FOR IMIDAZO[4,5-c]PYRIDIN-4-AMINES |
| US20050032829A1 (en) * | 2003-06-06 | 2005-02-10 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| US7445013B2 (en) | 2003-06-17 | 2008-11-04 | Whirlpool Corporation | Multiple wash zone dishwasher |
| KR20060054371A (ko) * | 2003-07-31 | 2006-05-22 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 캡슐화 및 제어된 방출을 위한 조성물 |
| AU2004264330A1 (en) * | 2003-08-05 | 2005-02-24 | 3M Innovative Properties Company | Infection prophylaxis using immune response modifier compounds |
| US8673932B2 (en) * | 2003-08-12 | 2014-03-18 | 3M Innovative Properties Company | Oxime substituted imidazo-containing compounds |
| WO2005018555A2 (en) * | 2003-08-14 | 2005-03-03 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
| US8961477B2 (en) * | 2003-08-25 | 2015-02-24 | 3M Innovative Properties Company | Delivery of immune response modifier compounds |
| US20050048072A1 (en) * | 2003-08-25 | 2005-03-03 | 3M Innovative Properties Company | Immunostimulatory combinations and treatments |
| AR045529A1 (es) * | 2003-08-27 | 2005-11-02 | 3M Innovative Properties Co | Imidazoquinolinas sustituidas con grupos ariloxi o arilalquilenoxi |
| EP1663222A4 (en) * | 2003-09-02 | 2008-05-21 | 3M Innovative Properties Co | METHODS RELATING TO THE TREATMENT OF GIANCES |
| EP1660026A4 (en) * | 2003-09-05 | 2008-07-16 | 3M Innovative Properties Co | TREATMENT FOR CD5 + B CELL LYMPHOMA |
| JP2007505629A (ja) * | 2003-09-17 | 2007-03-15 | スリーエム イノベイティブ プロパティズ カンパニー | Ｔｌｒ遺伝子発現の選択的調節 |
| WO2005030774A1 (en) * | 2003-09-26 | 2005-04-07 | Rigel Pharmaceuticals, Inc. | Hcv inhibitors and methods of using them |
| 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 |
| MY146124A (en) | 2003-10-03 | 2012-06-29 | 3M Innovative Properties Co | Pyrazolopyridines and analogs thereof |
| AR046046A1 (es) | 2003-10-03 | 2005-11-23 | 3M Innovative Properties Co | Imidazoquinolinas alcoxi sustituidas. composiciones farmaceuticas. |
| US20090075980A1 (en) * | 2003-10-03 | 2009-03-19 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and Analogs Thereof |
| US7544697B2 (en) * | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| AU2004285575A1 (en) * | 2003-10-31 | 2005-05-12 | 3M Innovative Properties Company | Neutrophil activation by immune response modifier compounds |
| CN1906192A (zh) | 2003-11-14 | 2007-01-31 | 3M创新有限公司 | 羟胺取代的咪唑环化合物 |
| WO2005048933A2 (en) * | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
| WO2005051324A2 (en) | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| AU2004293078B2 (en) * | 2003-11-25 | 2012-01-19 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| US20050226878A1 (en) * | 2003-12-02 | 2005-10-13 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
| WO2005055932A2 (en) * | 2003-12-02 | 2005-06-23 | 3M Innovative Properties Company | Therapeutic combinations and methods including irm compounds |
| CA2549216A1 (en) * | 2003-12-04 | 2005-08-25 | 3M Innovative Properties Company | Sulfone substituted imidazo ring ethers |
| US8802853B2 (en) * | 2003-12-29 | 2014-08-12 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| EP1699792A1 (en) * | 2003-12-29 | 2006-09-13 | 3M Innovative Properties Company | Piperazine, 1,4¨diazepane, 1,4¨diazocane, and 1,5¨diazocane fused imidazo ring compounds |
| EP1699398A4 (en) * | 2003-12-30 | 2007-10-17 | 3M Innovative Properties Co | IMPROVING THE IMMUNE RESPONSE |
| AU2004312508A1 (en) * | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| US20050201959A1 (en) * | 2004-03-11 | 2005-09-15 | Vvii Newco 2003, Inc. | Methods and compositions for altering skin coloration |
| CA2559607C (en) * | 2004-03-15 | 2013-02-19 | 3M Innovative Properties Company | Immune response modifier formulations and methods |
| WO2005094531A2 (en) * | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| JP2007532572A (ja) * | 2004-04-09 | 2007-11-15 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫反応調整剤を送達させるための方法、組成物および調製物 |
| EP1755665A4 (en) * | 2004-04-28 | 2010-03-03 | 3M Innovative Properties Co | COMPOSITIONS AND METHODS FOR MUCOSAL VACCINATION |
| US20050267145A1 (en) * | 2004-05-28 | 2005-12-01 | Merrill Bryon A | Treatment for lung cancer |
| US7569580B2 (en) | 2004-06-03 | 2009-08-04 | Rigel Pharmaceuticals, Inc. | Heterotricyclic compounds for use as HCV inhibitors |
| WO2005123079A2 (en) * | 2004-06-14 | 2005-12-29 | 3M Innovative Properties Company | Urea substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005123080A2 (en) * | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US7897609B2 (en) * | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| WO2006009826A1 (en) * | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| JP5128940B2 (ja) * | 2004-06-18 | 2013-01-23 | スリーエム イノベイティブ プロパティズ カンパニー | 置換イミダゾキノリン、イミダゾピリジン、およびイミダゾナフチリジン |
| US7915281B2 (en) * | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| ITMI20041282A1 (it) * | 2004-06-24 | 2004-09-24 | Dipharma Spa | Procedimento per la preparazione di imiquimod |
| US20060045886A1 (en) * | 2004-08-27 | 2006-03-02 | Kedl Ross M | HIV immunostimulatory compositions |
| WO2006026760A2 (en) * | 2004-09-02 | 2006-03-09 | 3M Innovative Properties Company | 1-amino imidazo-containing compounds and methods |
| AU2005282726B2 (en) * | 2004-09-02 | 2011-06-02 | 3M Innovative Properties Company | 1-alkoxy 1H-imidazo ring systems and methods |
| WO2006029115A2 (en) | 2004-09-02 | 2006-03-16 | 3M Innovative Properties Company | 2-amino 1h imidazo ring systems and methods |
| WO2006029223A2 (en) * | 2004-09-08 | 2006-03-16 | Children's Medical Center Corporation | Method for stimulating the immune response of newborns |
| EP1804583A4 (en) * | 2004-10-08 | 2009-05-20 | 3M Innovative Properties Co | ADJUVANT FOR DNA VACCINE |
| WO2006063072A2 (en) * | 2004-12-08 | 2006-06-15 | 3M Innovative Properties Company | Immunomodulatory compositions, combinations and methods |
| US7943609B2 (en) | 2004-12-30 | 2011-05-17 | 3M Innovative Proprerties Company | Chiral fused [1,2]imidazo[4,5-C] ring compounds |
| EP1833479A2 (en) * | 2004-12-30 | 2007-09-19 | Takeda Pharmaceutical Company Limited | 1-(2-methylpropyl)-1h-imidazo 4,5-c(1,5 )naphthyridin-4-amine ethanesulfonate and 1-(2-methylpropyl)-1h-imidazoý4,5-c 1,5 naphthyridin-4-amine methanesulfonate |
| EP2394650A1 (en) * | 2004-12-30 | 2011-12-14 | 3M Innovative Properties Co. | Use of resiquimod for the treatment of cutaneous metastases |
| US8436176B2 (en) * | 2004-12-30 | 2013-05-07 | Medicis Pharmaceutical Corporation | Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine |
| CA2594674C (en) | 2004-12-30 | 2016-05-17 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| EP1844201B1 (en) | 2005-02-04 | 2016-08-24 | 3M Innovative Properties Company | Aqueous gel formulations containing immune response modifiers |
| US20080318998A1 (en) * | 2005-02-09 | 2008-12-25 | Coley Pharmaceutical Group, Inc. | Alkyloxy Substituted Thiazoloquinolines and Thiazolonaphthyridines |
| AU2006338521A1 (en) | 2005-02-09 | 2007-10-11 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazolo(4,5-c) ring compounds and methods |
| WO2006091394A2 (en) * | 2005-02-11 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Substituted imidazoquinolines and imidazonaphthyridines |
| EP1846405A2 (en) | 2005-02-11 | 2007-10-24 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted imidazo 4,5-c ring compounds and methods |
| AU2006216798A1 (en) * | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
| CA2598639A1 (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 |
| CA2598695A1 (en) * | 2005-02-23 | 2006-09-21 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinolines |
| CA2602098A1 (en) | 2005-03-14 | 2006-09-21 | Graceway Pharmaceuticals, Llc | Method of treating actinic keratosis |
| PT1879893E (pt) * | 2005-03-21 | 2010-09-02 | Ferrer Int | Método de síntese de compostos da 1h-imidaz0[4,5-c]quinolin- 4-amina 1-substituída e intermediários dos mesmos |
| 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 |
| AU2006241166A1 (en) * | 2005-04-25 | 2006-11-02 | 3M Innovative Properties Company | Immunostimulatory compositions |
| CN101304748A (zh) * | 2005-08-22 | 2008-11-12 | 加利福尼亚大学董事会 | Tlr激动剂 |
| 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 |
| BRPI0615788A2 (pt) * | 2005-09-09 | 2011-05-24 | Coley Pharm Group Inc | derivados de amida e carbamato de n-{2-[4-amino (etoximetil)-1h-imidazo [4,5-c] quinolin-1-il]-1,1-dimetiletil} metanossulfonamida, composição farmacêutica destes e seus usos |
| US20070081962A1 (en) * | 2005-10-06 | 2007-04-12 | Amit Munshi | Novel delivery of immune response modifiers for removal of chronic tattoos |
| US20070100146A1 (en) * | 2005-11-03 | 2007-05-03 | Trevor Dzwiniel | Process for the preparation of imidazo[4,5-c]-quinolin-4-amines |
| KR20080083270A (ko) | 2005-11-04 | 2008-09-17 | 콜레이 파마시티컬 그룹, 인코포레이티드 | 하이드록시 및 알콕시 치환된 1에이치 이미다조퀴놀린 및방법 |
| WO2007100634A2 (en) | 2006-02-22 | 2007-09-07 | 3M Innovative Properties Company | Immune response modifier conjugates |
| WO2007106854A2 (en) * | 2006-03-15 | 2007-09-20 | Coley Pharmaceutical Group, Inc. | Hydroxy and alkoxy substituted 1h-imidazonaphthyridines and methods |
| WO2007142755A2 (en) | 2006-05-31 | 2007-12-13 | The Regents Of The University Of California | Purine analogs |
| 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 |
| US8178539B2 (en) * | 2006-09-06 | 2012-05-15 | 3M Innovative Properties Company | Substituted 3,4,6,7-tetrahydro-5H-1,2a,4a,8-tetraazacyclopenta[cd]phenalenes and methods |
| US20080149123A1 (en) * | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
| ES2456964T3 (es) | 2007-02-07 | 2014-04-24 | The Regents Of The University Of California | Conjugados de agonistas de TLR sintéticos y usos de los mismos |
| EP2009002A1 (en) * | 2007-06-21 | 2008-12-31 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | New process for the manufacture of 1H-imidazo [4,5-c]-quinoline ring systems |
| EP2259788A4 (en) * | 2008-02-07 | 2011-03-16 | Univ California | TREATMENT OF BLADDER DISEASES WITH A TLR7 ACTIVATOR |
| WO2010088924A1 (en) | 2009-02-06 | 2010-08-12 | Telormedix Sa | Pharmaceutical compositions comprising imidazoquinolin(amines) and derivatives thereof suitable for local administration |
| EA019768B1 (ru) * | 2009-02-11 | 2014-06-30 | Дзе Регентс Оф Дзе Юниверсити Оф Калифорния | СОЕДИНЕНИЯ, МОДУЛИРУЮЩИЕ АКТИВНОСТЬ Toll-ПОДОБНЫХ РЕЦЕПТОРОВ |
| US20110033515A1 (en) * | 2009-08-04 | 2011-02-10 | Rst Implanted Cell Technology | Tissue contacting material |
| LT2606047T (lt) | 2010-08-17 | 2017-04-10 | 3M Innovative Properties Company | Imuninio atsako modifikatoriaus junginio lipidizuotos kompozicijos, sudėtys ir būdai |
| EP3153180A1 (en) | 2011-06-03 | 2017-04-12 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| CA2838158C (en) | 2011-06-03 | 2019-07-16 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| US20130023736A1 (en) | 2011-07-21 | 2013-01-24 | Stanley Dale Harpstead | Systems for drug delivery and monitoring |
| CN104284674A (zh) | 2012-05-04 | 2015-01-14 | 辉瑞公司 | 前列腺相关抗原及基于疫苗的免疫治疗疗法 |
| US11697851B2 (en) | 2016-05-24 | 2023-07-11 | The Regents Of The University Of California | Early ovarian cancer detection diagnostic test based on mRNA isoforms |
| JP7197244B2 (ja) | 2017-12-20 | 2022-12-27 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節剤として使用するための分岐鎖連結基を有するアミド置換イミダゾ［４，５－ｃ］キノリン化合物 |
Family Cites Families (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3314941A (en) | 1964-06-23 | 1967-04-18 | American Cyanamid Co | Novel substituted pyridodiazepins |
| US3891653A (en) * | 1970-07-08 | 1975-06-24 | Lilly Co Eli | Substituted 4-5 dehydro-tetrazolo(1,5-a)quinolenes |
| US3764681A (en) * | 1970-07-08 | 1973-10-09 | Lilly Co Eli | Certain tetrazolo-(1,5-a) quinoline compounds as fungus control agents |
| 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 |
| US5035420A (en) * | 1988-11-28 | 1991-07-30 | Therabite Corporation | Jaw exerciser |
| 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 |
| DE69029212T2 (de) * | 1989-02-27 | 1997-05-22 | Riker Laboratories Inc | 4-Amino-1H-Imidazo(4,5-c)chinoline als antivirale Mittel |
| 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 |
| WO1992006093A1 (en) * | 1990-10-05 | 1992-04-16 | Minnesota Mining And Manufacturing Company | Process for the preparation of imidazo[4,5-c]quinolin-4-amines |
| US5175296A (en) * | 1991-03-01 | 1992-12-29 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]quinolin-4-amines and processes for their preparation |
| 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 |
| 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 |
| US5352784A (en) | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| KR100341341B1 (ko) | 1993-07-15 | 2002-11-25 | 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 | 이미다조[4,5-c]피리딘-4-아민 |
| US5482936A (en) | 1995-01-12 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-C]quinoline amines |
| US5544161A (en) * | 1995-03-28 | 1996-08-06 | Bell Atlantic Network Services, Inc. | ATM packet demultiplexer for use in full service network having distributed architecture |
| US5684799A (en) * | 1995-03-28 | 1997-11-04 | Bell Atlantic Network Services, Inc. | Full service network having distributed architecture |
| 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 |
| JPH09255926A (ja) | 1996-03-26 | 1997-09-30 | Diatex Co Ltd | 粘着テープ |
| US6021158A (en) * | 1996-05-09 | 2000-02-01 | Texas Instruments Incorporated | Hybrid wireless wire-line network integration and management |
| 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 |
| AU724042B2 (en) | 1996-10-25 | 2000-09-07 | Minnesota Mining And Manufacturing Company | Immune response modifier compounds for treatment of TH2 mediated and related diseases |
| 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 |
| 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 |
| JPH11255926A (ja) | 1998-03-13 | 1999-09-21 | Toray Ind Inc | シリコーン成型品およびその製造方法 |
| 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 |
| US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| US6245776B1 (en) | 1999-01-08 | 2001-06-12 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| 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 |
| US6331539B1 (en) | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6451810B1 (en) | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| 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 |
| US6660735B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| UA74593C2 (en) | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
| UA74852C2 (en) | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
| US6660747B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6664260B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Heterocyclic ether substituted imidazoquinolines |
| US6677347B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| AU3249802A (en) | 2000-12-08 | 2002-06-18 | 3M Innovative Properties Co | Screening method for identifying compounds that selectively induce interferon alpha |
| 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 |
| US6664265B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6667312B2 (en) | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| EP1401437A1 (en) | 2001-06-15 | 2004-03-31 | 3M Innovative Properties Company | Immune response modifiers for the treatment of periodontal disease |
-
1996
- 1996-06-21 US US08/673,712 patent/US5741908A/en not_active Expired - Lifetime
- 1996-10-22 KR KR10-2004-7003623A patent/KR20040029475A/ko not_active Withdrawn
- 1996-10-22 PT PT96946380T patent/PT912565E/pt unknown
- 1996-10-22 WO PCT/US1996/016972 patent/WO1997048704A1/en not_active Ceased
- 1996-10-22 ES ES96946380T patent/ES2215203T3/es not_active Expired - Lifetime
- 1996-10-22 NZ NZ333169A patent/NZ333169A/xx not_active IP Right Cessation
- 1996-10-22 AU AU39565/97A patent/AU721036B2/en not_active Ceased
- 1996-10-22 KR KR10-2004-7003625A patent/KR20040029476A/ko not_active Withdrawn
- 1996-10-22 AT AT96946380T patent/ATE264326T1/de active
- 1996-10-22 CA CA002257846A patent/CA2257846C/en not_active Expired - Fee Related
- 1996-10-22 DK DK96946380T patent/DK0912565T3/da active
- 1996-10-22 IL IL14831896A patent/IL148318A0/xx active IP Right Grant
- 1996-10-22 DE DE69632207T patent/DE69632207T2/de not_active Expired - Lifetime
- 1996-10-22 JP JP50289898A patent/JP4139915B2/ja not_active Expired - Fee Related
- 1996-10-22 EP EP96946380A patent/EP0912565B1/en not_active Expired - Lifetime
- 1996-10-22 IL IL12734896A patent/IL127348A/en not_active IP Right Cessation
- 1996-10-22 KR KR10-2004-7003626A patent/KR20040029477A/ko not_active Withdrawn
-
1997
- 1997-10-14 IL IL12734897A patent/IL127348A0/xx active IP Right Grant
-
1998
- 1998-04-16 US US09/061,401 patent/US5998619A/en not_active Expired - Lifetime
- 1998-12-18 NO NO986002A patent/NO316564B1/no not_active IP Right Cessation
-
1999
- 1999-08-17 US US09/375,587 patent/US6150523A/en not_active Expired - Lifetime
-
2000
- 2000-10-04 US US09/678,192 patent/US6437131B1/en not_active Expired - Lifetime
-
2002
- 2002-02-21 IL IL148318A patent/IL148318A/en not_active IP Right Cessation
- 2002-06-26 US US10/180,678 patent/US6534654B2/en not_active Expired - Lifetime
- 2002-10-01 IL IL152039A patent/IL152039A/en not_active IP Right Cessation
-
2003
- 2003-01-28 US US10/352,606 patent/US6613902B2/en not_active Expired - Lifetime
- 2003-02-06 US US10/360,210 patent/US6624305B2/en not_active Expired - Lifetime
- 2003-05-12 NO NO20032134A patent/NO318095B1/no not_active IP Right Cessation
- 2003-05-12 NO NO20032133A patent/NO318213B1/no not_active IP Right Cessation
- 2003-05-12 NO NO20032132A patent/NO318094B1/no not_active IP Right Cessation
- 2003-07-21 US US10/624,014 patent/US6897314B2/en not_active Expired - Fee Related
-
2004
- 2004-10-27 US US10/974,258 patent/US7026482B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO316564B1 (no) | Fremgangsmåte til fremstilling av imidazokinolinaminer | |
| US5395937A (en) | Process for preparing quinoline amines | |
| EP0912564B1 (en) | Process for preparing tetrahydroimidazoquinolinamines | |
| KR100459583B1 (ko) | 이미다조퀴놀린아민류의제조방법 | |
| IL152040A (en) | 4 - triphenylphosphinylamino - 1h - imidazo [4,5-c] quinolines, their preparation and use as intermediates in processes for preparing 1h - imidazo [4,5-c] quinolin - 4 - amines | |
| HU220667B1 (hu) | 1- és 2-helyzetben szubsztituált 1H-imidazo[4,5-c]kinolin-4-amin-származékok előállításában alkalmazható kinolinszármazékok | |
| KR20000016782A (ko) | 테트라히드로이미다조퀴놀린아민의 제조 방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |