CA2390163A1 - Dye labeled imidazoquinoline compounds - Google Patents
Dye labeled imidazoquinoline compounds Download PDFInfo
- Publication number
- CA2390163A1 CA2390163A1 CA002390163A CA2390163A CA2390163A1 CA 2390163 A1 CA2390163 A1 CA 2390163A1 CA 002390163 A CA002390163 A CA 002390163A CA 2390163 A CA2390163 A CA 2390163A CA 2390163 A1 CA2390163 A1 CA 2390163A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- carbon atoms
- amino
- alkyl
- halo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 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 abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 239000000975 dye Substances 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- -1 aralkenyl Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000006850 spacer group Chemical group 0.000 claims description 11
- 239000007850 fluorescent dye Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
- 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000006196 aroyl alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005335 azido alkyl group Chemical group 0.000 claims description 3
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- MPLHNVLQVRSVEE-UHFFFAOYSA-N texas red Chemical compound [O-]S(=O)(=O)C1=CC(S(Cl)(=O)=O)=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 MPLHNVLQVRSVEE-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- VFTLXHXYGQSOEN-UHFFFAOYSA-N 1h-imidazo[4,5-b][1,8]naphthyridine Chemical compound C1=CN=C2NC3=NC=NC3=CC2=C1 VFTLXHXYGQSOEN-UHFFFAOYSA-N 0.000 abstract description 7
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 230000028993 immune response Effects 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 210000004027 cell Anatomy 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 17
- 102000004127 Cytokines Human genes 0.000 description 16
- 108090000695 Cytokines Proteins 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 102000014150 Interferons Human genes 0.000 description 11
- 108010050904 Interferons Proteins 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 229940079322 interferon Drugs 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 8
- 125000001475 halogen functional group Chemical group 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 102000003390 tumor necrosis factor Human genes 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 102100040247 Tumor necrosis factor Human genes 0.000 description 7
- 230000006698 induction Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 5
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- YOIPACJXEXJZDL-UHFFFAOYSA-N 1-(2-aminoethyl)-2-(ethoxymethyl)imidazo[4,5-c]quinolin-4-amine;trihydrochloride Chemical group Cl.Cl.Cl.C1=CC=CC2=C(N(C(COCC)=N3)CCN)C3=C(N)N=C21 YOIPACJXEXJZDL-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 210000000601 blood cell Anatomy 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 210000000265 leukocyte Anatomy 0.000 description 4
- 210000001616 monocyte Anatomy 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000004866 1,1-dimethylethylcarbonyl group Chemical group CC(C)(C(=O)*)C 0.000 description 3
- YETCZFGQAKYIEX-UHFFFAOYSA-N 1-(2-aminoethyl)-2-butylimidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CCCC)=N3)CCN)C3=C(N)N=C21 YETCZFGQAKYIEX-UHFFFAOYSA-N 0.000 description 3
- CDRXULFWJQDMKB-UHFFFAOYSA-N 1-(4-aminobutyl)-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-4-amine Chemical group C1=CC=CC2=C(N(C(CCOC)=N3)CCCCN)C3=C(N)N=C21 CDRXULFWJQDMKB-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 238000002965 ELISA Methods 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 238000004166 bioassay Methods 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000000432 density-gradient centrifugation Methods 0.000 description 3
- 239000012091 fetal bovine serum Substances 0.000 description 3
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229960002751 imiquimod Drugs 0.000 description 3
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 3
- 239000002955 immunomodulating agent Substances 0.000 description 3
- 229940121354 immunomodulator Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- NYTKFKFUDXTEBS-UHFFFAOYSA-N 2-[(3-nitroquinolin-4-yl)amino]ethanol Chemical compound C1=CC=C2C(NCCO)=C([N+]([O-])=O)C=NC2=C1 NYTKFKFUDXTEBS-UHFFFAOYSA-N 0.000 description 2
- JWRNUPCIPGBNGE-UHFFFAOYSA-N 2-[2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]ethanol Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CCO)C3=CN=C21 JWRNUPCIPGBNGE-UHFFFAOYSA-N 0.000 description 2
- LQRYIPGCBAUCJS-UHFFFAOYSA-N 2-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]ethanol Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CCO)C3=C(N)N=C21 LQRYIPGCBAUCJS-UHFFFAOYSA-N 0.000 description 2
- DTUJLHXCBYJJAW-UHFFFAOYSA-N 5-[2-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)ethylcarbamothioylamino]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid Chemical compound C12=CC=C(O)C=C2OC2=CC(=O)C=CC2=C1C(C(=C1)C(O)=O)=CC=C1NC(=S)NCCN1C2=C3C=CC=CC3=NC(N)=C2N=C1CCCC DTUJLHXCBYJJAW-UHFFFAOYSA-N 0.000 description 2
- 238000008157 ELISA kit Methods 0.000 description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- 229930182816 L-glutamine Natural products 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 239000012980 RPMI-1640 medium Substances 0.000 description 2
- QTENRWWVYAAPBI-YZTFXSNBSA-N Streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@H]1[C@H](N=C(N)N)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@H]1[C@H](N=C(N)N)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]1O QTENRWWVYAAPBI-YZTFXSNBSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 239000012228 culture supernatant Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000000120 cytopathologic effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000000684 flow cytometry Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 2
- 238000004896 high resolution mass spectrometry Methods 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 229940124669 imidazoquinoline Drugs 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000010829 isocratic elution Methods 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000003068 molecular probe Substances 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- NTENRZPBDRWGSB-UHFFFAOYSA-N tert-butyl n-[2-(2-butylimidazo[4,5-c]quinolin-1-yl)ethyl]carbamate Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCNC(=O)OC(C)(C)C)C3=CN=C21 NTENRZPBDRWGSB-UHFFFAOYSA-N 0.000 description 2
- FZMGWVXUINEMBN-UHFFFAOYSA-N tert-butyl n-[2-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)ethyl]carbamate Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCNC(=O)OC(C)(C)C)C3=C(N)N=C21 FZMGWVXUINEMBN-UHFFFAOYSA-N 0.000 description 2
- OTKLQDFWRCZMQI-UHFFFAOYSA-N tert-butyl n-[4-[2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]carbamate Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCCNC(=O)OC(C)(C)C)C3=CN=C21 OTKLQDFWRCZMQI-UHFFFAOYSA-N 0.000 description 2
- DFQBHHGRVDQSFI-UHFFFAOYSA-N tert-butyl n-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]carbamate Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCCNC(=O)OC(C)(C)C)C3=C(N)N=C21 DFQBHHGRVDQSFI-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
- C09B11/08—Phthaleins; Phenolphthaleins; Fluorescein
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6863—Cytokines, i.e. immune system proteins modifying a biological response such as cell growth proliferation or differentiation, e.g. TNF, CNF, GM-CSF, lymphotoxin, MIF or their receptors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Cell Biology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Pathology (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Food Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16372499P | 1999-11-05 | 1999-11-05 | |
| US60/163,724 | 1999-11-05 | ||
| US09/705,072 US6376669B1 (en) | 1999-11-05 | 2000-11-02 | Dye labeled imidazoquinoline compounds |
| US09/705,072 | 2000-11-02 | ||
| PCT/US2000/030366 WO2001034709A1 (en) | 1999-11-05 | 2000-11-03 | Dye labeled imidazoquinoline compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2390163A1 true CA2390163A1 (en) | 2001-05-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002390163A Abandoned CA2390163A1 (en) | 1999-11-05 | 2000-11-03 | Dye labeled imidazoquinoline compounds |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US6376669B1 (enExample) |
| EP (1) | EP1228147B1 (enExample) |
| JP (1) | JP2004500347A (enExample) |
| AT (1) | ATE258963T1 (enExample) |
| AU (1) | AU1756601A (enExample) |
| CA (1) | CA2390163A1 (enExample) |
| DE (1) | DE60008133T2 (enExample) |
| DK (1) | DK1228147T3 (enExample) |
| ES (1) | ES2211650T3 (enExample) |
| NO (1) | NO20021974L (enExample) |
| PT (1) | PT1228147E (enExample) |
| WO (1) | WO2001034709A1 (enExample) |
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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 |
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| 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 |
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| US6573273B1 (en) * | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| 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 |
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| US7226928B2 (en) * | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
| JP2005501550A (ja) * | 2001-08-30 | 2005-01-20 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫反応調整剤分子を用いた形質細胞様樹状細胞を成熟させる方法 |
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| EP1450804B9 (en) * | 2001-11-29 | 2009-04-01 | 3M Innovative Properties Company | Pharmaceutical formulations comprising an immune response modifier |
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| EP1478327B1 (en) * | 2002-02-22 | 2015-04-29 | Meda AB | Method of reducing and treating uvb-induced immunosuppression |
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| US5585612A (en) | 1995-03-20 | 1996-12-17 | Harp Enterprises, Inc. | Method and apparatus for voting |
| 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 |
| 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 |
| WO1998015564A1 (en) * | 1996-10-08 | 1998-04-16 | Kreatech Biotechnology B.V. | Methods for labeling nucleotides, labeled nucleotides and useful intermediates |
| CZ294563B6 (cs) | 1996-10-25 | 2005-02-16 | Minnesota Mining And Manufacturing Company | Sloučeniny představující modifikátory imunitní odezvy při léčení nemocí mediovaných TH2 buňkami a nemocí odvozených |
| US5939090A (en) | 1996-12-03 | 1999-08-17 | 3M Innovative Properties Company | Gel formulations for topical drug delivery |
| US6069149A (en) | 1997-01-09 | 2000-05-30 | Terumo Kabushiki Kaisha | Amide derivatives and intermediates for the synthesis thereof |
| ATE284407T1 (de) * | 1997-11-07 | 2004-12-15 | Isis Pharmaceuticals Inc | Pyrimidinderivate als markierte bindungspartner |
| 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 |
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| 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 |
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-
2000
- 2000-11-02 US US09/705,072 patent/US6376669B1/en not_active Expired - Fee Related
- 2000-11-03 ES ES00980282T patent/ES2211650T3/es not_active Expired - Lifetime
- 2000-11-03 WO PCT/US2000/030366 patent/WO2001034709A1/en not_active Ceased
- 2000-11-03 AT AT00980282T patent/ATE258963T1/de not_active IP Right Cessation
- 2000-11-03 JP JP2001537411A patent/JP2004500347A/ja active Pending
- 2000-11-03 EP EP00980282A patent/EP1228147B1/en not_active Expired - Lifetime
- 2000-11-03 AU AU17566/01A patent/AU1756601A/en not_active Abandoned
- 2000-11-03 DK DK00980282T patent/DK1228147T3/da active
- 2000-11-03 DE DE60008133T patent/DE60008133T2/de not_active Expired - Fee Related
- 2000-11-03 PT PT00980282T patent/PT1228147E/pt unknown
- 2000-11-03 CA CA002390163A patent/CA2390163A1/en not_active Abandoned
-
2002
- 2002-02-19 US US10/078,645 patent/US6630588B2/en not_active Expired - Fee Related
- 2002-04-25 NO NO20021974A patent/NO20021974L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004500347A (ja) | 2004-01-08 |
| DK1228147T3 (da) | 2004-05-10 |
| US20020120141A1 (en) | 2002-08-29 |
| AU1756601A (en) | 2001-06-06 |
| US6630588B2 (en) | 2003-10-07 |
| ATE258963T1 (de) | 2004-02-15 |
| NO20021974L (no) | 2002-06-28 |
| ES2211650T3 (es) | 2004-07-16 |
| DE60008133T2 (de) | 2004-09-16 |
| DE60008133D1 (de) | 2004-03-11 |
| NO20021974D0 (no) | 2002-04-25 |
| EP1228147B1 (en) | 2004-02-04 |
| EP1228147A1 (en) | 2002-08-07 |
| US6376669B1 (en) | 2002-04-23 |
| WO2001034709A1 (en) | 2001-05-17 |
| PT1228147E (pt) | 2004-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |