IL114570A - Compounds H1 – imidazo] C – 4,5 [quinoline - Google Patents
Compounds H1 – imidazo] C – 4,5 [quinolineInfo
- Publication number
- IL114570A IL114570A IL11457092A IL11457092A IL114570A IL 114570 A IL114570 A IL 114570A IL 11457092 A IL11457092 A IL 11457092A IL 11457092 A IL11457092 A IL 11457092A IL 114570 A IL114570 A IL 114570A
- Authority
- IL
- Israel
- Prior art keywords
- carbon atoms
- imidazo
- methylpropyl
- mixture
- solid
- Prior art date
Links
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- -1 alkylamido Chemical group 0.000 claims abstract description 28
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 4
- 125000005333 aroyloxy group Chemical group 0.000 claims description 4
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 4
- GIIWGCBLYNDKBO-UHFFFAOYSA-N Quinoline 1-oxide Chemical class C1=CC=C2[N+]([O-])=CC=CC2=C1 GIIWGCBLYNDKBO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 12
- 102000014150 Interferons Human genes 0.000 abstract 1
- 108010050904 Interferons Proteins 0.000 abstract 1
- 238000010171 animal model Methods 0.000 abstract 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229940079322 interferon Drugs 0.000 abstract 1
- 230000005740 tumor formation Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 186
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 183
- 239000007787 solid Substances 0.000 description 124
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 106
- 239000000203 mixture Substances 0.000 description 99
- 239000000047 product Substances 0.000 description 74
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 62
- 238000004458 analytical method Methods 0.000 description 61
- 239000000243 solution Substances 0.000 description 58
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 53
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 38
- 238000007429 general method Methods 0.000 description 38
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 31
- 235000019341 magnesium sulphate Nutrition 0.000 description 31
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
- 229910052799 carbon Inorganic materials 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 29
- 238000005481 NMR spectroscopy Methods 0.000 description 28
- 239000002244 precipitate Substances 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 20
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 19
- 239000000908 ammonium hydroxide Substances 0.000 description 19
- 239000012043 crude product Substances 0.000 description 19
- 239000003921 oil Substances 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 239000003480 eluent Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000000523 sample Substances 0.000 description 11
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- HREHOXSRYOZKNT-UHFFFAOYSA-N quinolin-2-ylmethanol Chemical compound C1=CC=CC2=NC(CO)=CC=C21 HREHOXSRYOZKNT-UHFFFAOYSA-N 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- LHBODUUXCWHZLN-UHFFFAOYSA-N 1-[(3-aminoquinolin-4-yl)amino]-2-methylpropan-2-ol Chemical compound C1=CC=C2C(NCC(C)(O)C)=C(N)C=NC2=C1 LHBODUUXCWHZLN-UHFFFAOYSA-N 0.000 description 3
- SIEDJWXHTNOOMX-UHFFFAOYSA-N 1-benzyl-2-(chloromethyl)imidazo[4,5-c]quinolin-4-amine;hydrochloride Chemical compound Cl.ClCC1=NC=2C(N)=NC3=CC=CC=C3C=2N1CC1=CC=CC=C1 SIEDJWXHTNOOMX-UHFFFAOYSA-N 0.000 description 3
- ZWISCKSGNCMAQO-UHFFFAOYSA-N 3-nitro-1H-quinolin-4-one Chemical class C1=CC=C2C(=O)C([N+](=O)[O-])=CNC2=C1 ZWISCKSGNCMAQO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CXYOCSTZCULCAE-UHFFFAOYSA-N 1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=CN=C21 CXYOCSTZCULCAE-UHFFFAOYSA-N 0.000 description 2
- CMNBVGJQAZZTGK-UHFFFAOYSA-N 1-[1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]pentyl acetate Chemical compound C1=CC=CC2=C(N(C(C(OC(C)=O)CCCC)=N3)CC(C)C)C3=CN=C21 CMNBVGJQAZZTGK-UHFFFAOYSA-N 0.000 description 2
- CYOHXZCGGOMRPN-UHFFFAOYSA-N 1-benzyl-2-(ethoxymethyl)imidazo[4,5-c]quinoline Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC1=CC=CC=C1 CYOHXZCGGOMRPN-UHFFFAOYSA-N 0.000 description 2
- DZCWNQSANNLVLU-UHFFFAOYSA-N 2-(1-methoxyethyl)-1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(C(C)OC)=N3)CC(C)C)C3=CN=C21 DZCWNQSANNLVLU-UHFFFAOYSA-N 0.000 description 2
- BPWHKSURAHFCOK-UHFFFAOYSA-N 2-(2-methoxypropyl)-1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CC(C)OC)=N3)CC(C)C)C3=CN=C21 BPWHKSURAHFCOK-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZRFUZDDJSQVQBY-UHFFFAOYSA-N 4-chloro-3-nitroquinoline Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CN=C21 ZRFUZDDJSQVQBY-UHFFFAOYSA-N 0.000 description 2
- JFMKIQOIIMSWIM-UHFFFAOYSA-N 4-n-(2-methylpropyl)quinoline-3,4-diamine Chemical compound C1=CC=C2C(NCC(C)C)=C(N)C=NC2=C1 JFMKIQOIIMSWIM-UHFFFAOYSA-N 0.000 description 2
- HKGPTTMXHQAEBO-UHFFFAOYSA-N 4-n-benzylquinoline-3,4-diamine Chemical compound NC1=CN=C2C=CC=CC2=C1NCC1=CC=CC=C1 HKGPTTMXHQAEBO-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-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
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- OYVXVLSZQHSNDK-UHFFFAOYSA-N n-methoxy-n-methylacetamide Chemical compound CON(C)C(C)=O OYVXVLSZQHSNDK-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- MKBAIJABBHSFLO-UHFFFAOYSA-N 1-[(7-chloro-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol Chemical compound ClC1=CC=C2C(NCC(C)(O)C)=C([N+]([O-])=O)C=NC2=C1 MKBAIJABBHSFLO-UHFFFAOYSA-N 0.000 description 1
- CPVFCCNLDDNHEQ-UHFFFAOYSA-N 1-[1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]ethyl acetate Chemical compound C1=CC=CC2=C3N(CC(C)C)C(C(C)OC(C)=O)=NC3=CN=C21 CPVFCCNLDDNHEQ-UHFFFAOYSA-N 0.000 description 1
- PXPXISCMGOOWKY-UHFFFAOYSA-N 1-[1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]propan-2-one Chemical compound C1=CC=CC2=C3N(CC(C)C)C(CC(C)=O)=NC3=CN=C21 PXPXISCMGOOWKY-UHFFFAOYSA-N 0.000 description 1
- MYKUTOOCWPZANP-UHFFFAOYSA-N 1-[2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=CN=C21 MYKUTOOCWPZANP-UHFFFAOYSA-N 0.000 description 1
- PHQXGNCDUAGYFI-UHFFFAOYSA-N 1-[7-chloro-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(Cl)C=CC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=CN=C21 PHQXGNCDUAGYFI-UHFFFAOYSA-N 0.000 description 1
- XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 1
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 1
- QGKFIUDEXLBEEL-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CC(C)C)C3=CN=C21 QGKFIUDEXLBEEL-UHFFFAOYSA-N 0.000 description 1
- SNIIIYRLNGBHDQ-UHFFFAOYSA-N 2-(chloromethyl)-1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine;hydrochloride Chemical compound Cl.C1=CC=CC2=C3N(CC(C)C)C(CCl)=NC3=C(N)N=C21 SNIIIYRLNGBHDQ-UHFFFAOYSA-N 0.000 description 1
- YNWHCSUNJFFKPL-UHFFFAOYSA-N 2-(ethoxymethyl)-1-(3-methoxypropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CCCOC)C3=C(N)N=C21 YNWHCSUNJFFKPL-UHFFFAOYSA-N 0.000 description 1
- IHOSZIKZWNTQLG-UHFFFAOYSA-N 2-(ethoxymethyl)-1-(3-methoxypropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CCCOC)C3=CN=C21 IHOSZIKZWNTQLG-UHFFFAOYSA-N 0.000 description 1
- GSAPQQLGLZGQPF-UHFFFAOYSA-N 2-(methoxymethyl)-1-(2-methylpropyl)imidazo[4,5-c]quinoline hydrate Chemical compound CC(C)CN1C(=NC2=C1C3=CC=CC=C3N=C2)COC.O GSAPQQLGLZGQPF-UHFFFAOYSA-N 0.000 description 1
- XLPAQTSMTCHNKW-UHFFFAOYSA-N 2-[methoxy(phenyl)methyl]-1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical compound N=1C2=CN=C3C=CC=CC3=C2N(CC(C)C)C=1C(OC)C1=CC=CC=C1 XLPAQTSMTCHNKW-UHFFFAOYSA-N 0.000 description 1
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
- QUGBHIZCLVAQOG-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CC(C)C)C(C)=NC3=CN=C21 QUGBHIZCLVAQOG-UHFFFAOYSA-N 0.000 description 1
- 125000004892 2-methylpropylamino group Chemical group CC(CN*)C 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- ZCVZBMGSTIUGRP-UHFFFAOYSA-N 7-chloro-3-nitro-1h-quinolin-4-one Chemical compound ClC1=CC=C2C(=O)C([N+](=O)[O-])=CNC2=C1 ZCVZBMGSTIUGRP-UHFFFAOYSA-N 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- GXKQCECUGSBCSG-UHFFFAOYSA-N S(=O)(Cl)Cl.N1=CC=C(C2=CC=CC=C12)N Chemical compound S(=O)(Cl)Cl.N1=CC=C(C2=CC=CC=C12)N GXKQCECUGSBCSG-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 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 1
- UNFDPWJZANZQLO-UHFFFAOYSA-N [4-(4-chlorophenyl)-1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]methanol Chemical compound N1=C2C=CC=CC2=C2N(CC(C)C)C(CO)=NC2=C1C1=CC=C(Cl)C=C1 UNFDPWJZANZQLO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- CDUWBBGUDMBQDE-UHFFFAOYSA-N n-(2-methylpropyl)-3-nitroquinolin-4-amine Chemical compound C1=CC=C2C(NCC(C)C)=C([N+]([O-])=O)C=NC2=C1 CDUWBBGUDMBQDE-UHFFFAOYSA-N 0.000 description 1
- LXOCMSLRKNZDMY-UHFFFAOYSA-N n-(3-methoxypropyl)-3-nitroquinolin-4-amine Chemical compound C1=CC=C2C(NCCCOC)=C([N+]([O-])=O)C=NC2=C1 LXOCMSLRKNZDMY-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000010959 steel Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Lubricants (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66292691A | 1991-03-01 | 1991-03-01 | |
| US68732691A | 1991-04-18 | 1991-04-18 | |
| IL10111092A IL101110A (en) | 1991-03-01 | 1992-03-01 | H1-Amidazo] -C-4,5 [-Quinoline-4-Amines converted at position 2, pharmaceutical preparations containing them and certain intermediates new to them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL114570A0 IL114570A0 (en) | 1995-11-27 |
| IL114570A true IL114570A (en) | 1996-10-31 |
Family
ID=27098631
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11457092A IL114570A (en) | 1991-03-01 | 1992-03-01 | Compounds H1 – imidazo] C – 4,5 [quinoline |
| IL10111092A IL101110A (en) | 1991-03-01 | 1992-03-01 | H1-Amidazo] -C-4,5 [-Quinoline-4-Amines converted at position 2, pharmaceutical preparations containing them and certain intermediates new to them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10111092A IL101110A (en) | 1991-03-01 | 1992-03-01 | H1-Amidazo] -C-4,5 [-Quinoline-4-Amines converted at position 2, pharmaceutical preparations containing them and certain intermediates new to them |
Country Status (18)
| Country | Link |
|---|---|
| EP (2) | EP0582581B1 (cs) |
| JP (1) | JP2955019B2 (cs) |
| AT (2) | ATE179711T1 (cs) |
| AU (2) | AU658621B2 (cs) |
| CA (2) | CA2289219C (cs) |
| CZ (1) | CZ285050B6 (cs) |
| DE (2) | DE69232878T2 (cs) |
| DK (2) | DK0582581T3 (cs) |
| ES (2) | ES2186034T3 (cs) |
| HU (5) | HU222251B1 (cs) |
| IE (1) | IE920605A1 (cs) |
| IL (2) | IL114570A (cs) |
| NO (1) | NO303729B1 (cs) |
| NZ (1) | NZ241784A (cs) |
| PH (1) | PH31614A (cs) |
| SG (2) | SG46492A1 (cs) |
| UA (1) | UA32546C2 (cs) |
| WO (1) | WO1992015582A1 (cs) |
Families Citing this family (88)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5266575A (en) * | 1991-11-06 | 1993-11-30 | Minnesota Mining And Manufacturing Company | 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines |
| US5395937A (en) * | 1993-01-29 | 1995-03-07 | Minnesota Mining And Manufacturing Company | Process for preparing quinoline amines |
| US5648516A (en) * | 1994-07-20 | 1997-07-15 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| CA2167042A1 (en) * | 1993-07-15 | 1995-01-26 | Kyle J. Lindstrom | Imidazo[4,5-c]pyridin-4-amines |
| US5352784A (en) * | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| US5482936A (en) * | 1995-01-12 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-C]quinoline amines |
| US6133547A (en) * | 1996-09-05 | 2000-10-17 | Medtronic, Inc. | Distributed activator for a two-dimensional shape memory alloy |
| US5939090A (en) | 1996-12-03 | 1999-08-17 | 3M Innovative Properties Company | Gel formulations for topical drug delivery |
| JPH10298181A (ja) * | 1997-04-25 | 1998-11-10 | Sumitomo Pharmaceut Co Ltd | タイプ２ヘルパーｔ細胞選択的免疫応答抑制剤 |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| 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 |
| EP1541572A1 (en) * | 2000-12-08 | 2005-06-15 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| GB0211649D0 (en) | 2002-05-21 | 2002-07-03 | Novartis Ag | Organic compounds |
| KR20050028047A (ko) * | 2002-07-23 | 2005-03-21 | 비오갈 기오기스제르갸르 알티. | 1ｈ-이미다조[4,5-ｃ]퀴놀린-4-프탈이미드 중간체를 통한1ｈ-이미다조[4,5-ｃ]퀴놀린-4-아민의 제조 |
| JP5043435B2 (ja) | 2003-10-03 | 2012-10-10 | スリーエム イノベイティブ プロパティズ カンパニー | アルコキシ置換イミダゾキノリン |
| NZ547467A (en) | 2003-11-25 | 2010-06-25 | 3M Innovative Properties Co | Substituted imidazo ring system and methods |
| CA2571360C (en) * | 2004-06-18 | 2014-11-25 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines useful in inducing cytokine biosynthesis in animals |
| US8080560B2 (en) | 2004-12-17 | 2011-12-20 | 3M Innovative Properties Company | Immune response modifier formulations containing oleic acid and methods |
| AU2006210392A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune response modifiers |
| CA2601924A1 (en) | 2005-02-18 | 2006-08-24 | Novartis Vaccines And Diagnostics, Inc. | Proteins and nucleic acids from meningitis/sepsis-associated escherichia coli |
| US8062644B2 (en) | 2005-02-18 | 2011-11-22 | Novartis Vaccines & Diagnostics Srl. | Immunogens from uropathogenic Escherichia coli |
| CA2598695A1 (en) * | 2005-02-23 | 2006-09-21 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinolines |
| JP2008531567A (ja) | 2005-02-23 | 2008-08-14 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ヒドロキシアルキル置換イミダゾキノリン化合物および方法 |
| WO2006091647A2 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Method of preferentially inducing the biosynthesis of interferon |
| 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 |
| WO2007056112A2 (en) * | 2005-11-04 | 2007-05-18 | Coley Pharmaceutical Group, Inc. | Hydroxy and alkoxy substituted 1h-imidazoquinolines and methods |
| WO2007052155A2 (en) | 2005-11-04 | 2007-05-10 | Novartis Vaccines And Diagnostics Srl | Influenza vaccine with reduced amount of oil-in-water emulsion as adjuvant |
| CA2628328A1 (en) | 2005-11-04 | 2007-05-10 | Novartis Vaccines And Diagnostics S.R.L. | Influenza vaccines including combinations of particulate adjuvants and immunopotentiators |
| PL2368572T3 (pl) | 2005-11-04 | 2020-11-16 | Seqirus UK Limited | Szczepionki z adjuwantem z niewirionowymi antygenami otrzymane z wirusów grypy hodowanych w hodowli komórkowej |
| CA2628424A1 (en) | 2005-11-04 | 2007-05-10 | Novartis Vaccines And Diagnostics S.R.L. | Adjuvanted influenza vaccines including cytokine-inducing agents |
| JP6087041B2 (ja) | 2006-01-27 | 2017-03-08 | ノバルティス アーゲー | 血球凝集素およびマトリックスタンパク質を含むインフルエンザウイルスワクチン |
| US20100068223A1 (en) | 2006-03-24 | 2010-03-18 | Hanno Scheffczik | Storage of Influenza Vaccines Without Refrigeration |
| CA2647942A1 (en) | 2006-03-31 | 2007-11-08 | Novartis Ag | Combined mucosal and parenteral immunization against hiv |
| EP2054431B1 (en) | 2006-06-09 | 2011-08-31 | Novartis AG | Conformers of bacterial adhesins |
| GB0614460D0 (en) | 2006-07-20 | 2006-08-30 | Novartis Ag | Vaccines |
| AU2007279376B2 (en) | 2006-07-31 | 2012-09-06 | Wirra Ip Pty Ltd | Immune response modifier compositions and methods |
| JP2010500399A (ja) | 2006-08-16 | 2010-01-07 | ノバルティス アーゲー | 尿路病原性大腸菌由来の免疫原 |
| WO2008032219A2 (en) | 2006-09-11 | 2008-03-20 | Novartis Ag | Making influenza virus vaccines without using eggs |
| CA2671629C (en) | 2006-12-06 | 2017-08-15 | Novartis Ag | Vaccines including antigen from four strains of influenza virus |
| GB0700562D0 (en) | 2007-01-11 | 2007-02-21 | Novartis Vaccines & Diagnostic | Modified Saccharides |
| BRPI0811125A2 (pt) * | 2007-05-08 | 2017-05-09 | Astrazeneca Ab | imidazoquinolinas com propriedades imunomoduladoras |
| JP2010531348A (ja) | 2007-06-27 | 2010-09-24 | ノバルティス アーゲー | 添加剤の少ないインフルエンザワクチン |
| GB0714963D0 (en) | 2007-08-01 | 2007-09-12 | Novartis Ag | Compositions comprising antigens |
| GB0810305D0 (en) | 2008-06-05 | 2008-07-09 | Novartis Ag | Influenza vaccination |
| GB0818453D0 (en) | 2008-10-08 | 2008-11-12 | Novartis Ag | Fermentation processes for cultivating streptococci and purification processes for obtaining cps therefrom |
| MY150481A (en) * | 2008-03-03 | 2014-01-30 | Irm Llc | Compounds and compositions as tlr activity modulators |
| EP2889042A3 (en) | 2008-03-18 | 2015-10-14 | Novartis AG | Improvements in preparation of influenza virus vaccine antigens |
| CN103396415B (zh) * | 2008-03-24 | 2016-08-10 | 4Sc股份有限公司 | 新的取代的咪唑并喹啉化合物 |
| ES2733084T3 (es) | 2009-03-06 | 2019-11-27 | Glaxosmithkline Biologicals Sa | Antígenos de Chlamydia |
| MX2011010735A (es) | 2009-04-14 | 2012-01-25 | Novartis Ag | Composiciones para inmunizacion contra staphylococcus aureus. |
| EP2424565A1 (en) | 2009-04-27 | 2012-03-07 | Novartis AG | Adjuvanted vaccines for protecting against influenza |
| JP2012532600A (ja) | 2009-07-07 | 2012-12-20 | ノバルティス アーゲー | 保存された大腸菌免疫原 |
| CN102639147B (zh) | 2009-07-15 | 2015-11-25 | 诺华股份有限公司 | Rsv f 蛋白组合物和其制作方法 |
| ES2526996T3 (es) | 2009-07-16 | 2015-01-19 | Novartis Ag | Inmunógenos desintoxicados de Escherichia coli |
| GB0918392D0 (en) | 2009-10-20 | 2009-12-02 | Novartis Ag | Diagnostic and therapeutic methods |
| GB0919690D0 (en) | 2009-11-10 | 2009-12-23 | Guy S And St Thomas S Nhs Foun | compositions for immunising against staphylococcus aureus |
| WO2011084726A1 (en) * | 2009-12-21 | 2011-07-14 | 3M Innovative Properties Company | BIS [4-AMINO-2-(ETHOXYMETHYL)-1-(2-HYDROXY-2-METHYLPROPYL)-1H-IMIDAZO[4,5-c]QUINOLIN-5-IUM] 4-[(3-CARBOXYLATO-2-HYDROXYNAPHTHALEN-1-YL)METHYL]-3-HYDROXYNAPHTHALENE-2-CARBOXYLATE COMPOSITIONS AND METHODS |
| WO2011084725A1 (en) * | 2009-12-21 | 2011-07-14 | 3M Innovative Properties Company | 4-AMINO-2-(ETHOXYMETHYL)-1-(2-HYDROXY-2-METHYLPROPYL)-1H-IMIDAZO[4,5-c]QUINOLIN-5-IUM 1-HYDROXYNAPHTHALENE-2-CARBOXYLATE COMPOSITIONS AND METHODS |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CA1271477A (en) * | 1983-11-18 | 1990-07-10 | John F. Gerster | 1h-imidazo[4,5-c]quinolin-4-amines |
| DK0385630T3 (da) * | 1989-02-27 | 1997-05-12 | Riker Laboratories Inc | 1H-imidazo(4,5-c)quinolin-4-aminer som antivirale midler |
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1992
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