CA2594674C - Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds - Google Patents
Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds Download PDFInfo
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- CA2594674C CA2594674C CA2594674A CA2594674A CA2594674C CA 2594674 C CA2594674 C CA 2594674C CA 2594674 A CA2594674 A CA 2594674A CA 2594674 A CA2594674 A CA 2594674A CA 2594674 C CA2594674 C CA 2594674C
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- Prior art keywords
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- alkyl
- compound
- salt
- alkylene
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 358
- 102000004127 Cytokines Human genes 0.000 claims abstract description 44
- 108090000695 Cytokines Proteins 0.000 claims abstract description 44
- 241001465754 Metazoa Species 0.000 claims abstract description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
- 201000010099 disease Diseases 0.000 claims abstract description 30
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 230000003612 virological effect Effects 0.000 claims abstract description 12
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 210
- 125000003118 aryl group Chemical group 0.000 claims description 143
- 125000002947 alkylene group Chemical group 0.000 claims description 142
- 150000003839 salts Chemical class 0.000 claims description 133
- 125000001072 heteroaryl group Chemical group 0.000 claims description 121
- 125000000623 heterocyclic group Chemical group 0.000 claims description 114
- -1 arylalkylenyl Chemical group 0.000 claims description 113
- 125000003342 alkenyl group Chemical group 0.000 claims description 106
- 229910052739 hydrogen Inorganic materials 0.000 claims description 103
- 239000001257 hydrogen Substances 0.000 claims description 102
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 100
- 125000001424 substituent group Chemical group 0.000 claims description 93
- 125000004450 alkenylene group Chemical group 0.000 claims description 86
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 86
- 125000003545 alkoxy group Chemical group 0.000 claims description 84
- 229910052736 halogen Inorganic materials 0.000 claims description 74
- 125000000304 alkynyl group Chemical group 0.000 claims description 73
- 150000002367 halogens Chemical class 0.000 claims description 67
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 58
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 54
- 125000005466 alkylenyl group Chemical group 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
- 125000001188 haloalkyl group Chemical group 0.000 claims description 48
- 125000000732 arylene group Chemical group 0.000 claims description 35
- 125000004414 alkyl thio group Chemical group 0.000 claims description 32
- 125000005549 heteroarylene group Chemical group 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000004419 alkynylene group Chemical group 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 23
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 23
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 23
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 230000006698 induction Effects 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 7
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 abstract description 70
- 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 abstract description 17
- 239000000543 intermediate Substances 0.000 abstract description 16
- 150000001408 amides Chemical class 0.000 abstract description 13
- 150000002148 esters Chemical class 0.000 abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 9
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract description 6
- 125000000524 functional group Chemical group 0.000 abstract description 6
- 150000002576 ketones Chemical class 0.000 abstract description 6
- 239000004202 carbamide Substances 0.000 abstract description 5
- 230000001939 inductive effect Effects 0.000 abstract description 4
- 229940124530 sulfonamide Drugs 0.000 abstract description 4
- 150000003456 sulfonamides Chemical class 0.000 abstract description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 3
- 239000002955 immunomodulating agent Substances 0.000 abstract description 3
- 229940121354 immunomodulator Drugs 0.000 abstract description 3
- 150000002923 oximes Chemical class 0.000 abstract description 3
- QNLFZRVIACOXAG-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,8]naphthyridine Chemical class N1=CC=CC2=C(NC=N3)C3=CN=C21 QNLFZRVIACOXAG-UHFFFAOYSA-N 0.000 abstract 1
- VROCUHFCXAAFLK-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c][1,8]naphthyridine Chemical class C1=C2NC=NC2=C2CCCNC2=N1 VROCUHFCXAAFLK-UHFFFAOYSA-N 0.000 abstract 1
- CZTQJCYFLGFVLG-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c]quinoline Chemical class C1CCCC2=C1N=CC1=C2NC=N1 CZTQJCYFLGFVLG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
- 150000003457 sulfones Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 225
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- 239000000243 solution Substances 0.000 description 109
- 239000011541 reaction mixture Substances 0.000 description 97
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 90
- 230000002829 reductive effect Effects 0.000 description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- 239000007787 solid Substances 0.000 description 61
- 239000002904 solvent Substances 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
- 229910052799 carbon Inorganic materials 0.000 description 50
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 49
- 125000005842 heteroatom Chemical group 0.000 description 46
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 44
- 150000001721 carbon Chemical group 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 40
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
- 229910052757 nitrogen Inorganic materials 0.000 description 37
- 239000007832 Na2SO4 Substances 0.000 description 35
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 35
- 239000010410 layer Substances 0.000 description 35
- 229910052938 sodium sulfate Inorganic materials 0.000 description 35
- 235000011152 sodium sulphate Nutrition 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 238000004587 chromatography analysis Methods 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 30
- 239000012267 brine Substances 0.000 description 30
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 29
- 229910052720 vanadium Inorganic materials 0.000 description 29
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 28
- 125000005843 halogen group Chemical group 0.000 description 28
- 102100040247 Tumor necrosis factor Human genes 0.000 description 27
- 238000003756 stirring Methods 0.000 description 25
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
- 229910052717 sulfur Inorganic materials 0.000 description 23
- 239000003153 chemical reaction reagent Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000003396 thiol group Chemical class [H]S* 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 20
- 239000006260 foam Substances 0.000 description 20
- 125000004043 oxo group Chemical group O=* 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 17
- 239000000651 prodrug Substances 0.000 description 17
- 229940002612 prodrug Drugs 0.000 description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
- 235000011114 ammonium hydroxide Nutrition 0.000 description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 125000006239 protecting group Chemical group 0.000 description 16
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- 238000007796 conventional method Methods 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 14
- IDUUCDZKSKUCOP-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C(NC=N3)C3=CN=C21 IDUUCDZKSKUCOP-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 239000006188 syrup Substances 0.000 description 13
- 235000020357 syrup Nutrition 0.000 description 13
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 12
- 238000010189 synthetic method Methods 0.000 description 12
- 125000001589 carboacyl group Chemical group 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- YHEPBWTXCZVUHG-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-6-amine Chemical compound N1=C2C(N)=CC=CC2=C2NC=NC2=C1 YHEPBWTXCZVUHG-UHFFFAOYSA-N 0.000 description 10
- 125000004423 acyloxy group Chemical group 0.000 description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 125000005110 aryl thio group Chemical group 0.000 description 10
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 235000017550 sodium carbonate Nutrition 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 9
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 230000028993 immune response Effects 0.000 description 9
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 9
- MYDQAEQZZKVJSL-UHFFFAOYSA-N pentyl carbamate Chemical compound CCCCCOC(N)=O MYDQAEQZZKVJSL-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 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 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
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- 239000002158 endotoxin Substances 0.000 description 8
- 238000011534 incubation Methods 0.000 description 8
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- 239000000843 powder Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- MIDQVYLLSDOPIL-UHFFFAOYSA-N 1,5-naphthyridine-3,4-diamine Chemical compound C1=CC=NC2=C(N)C(N)=CN=C21 MIDQVYLLSDOPIL-UHFFFAOYSA-N 0.000 description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
- JMRGMXMLNCDPGG-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,5]naphthyridin-6-amine Chemical compound N1=C2C(N)=CC=NC2=C2NC=NC2=C1 JMRGMXMLNCDPGG-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 7
- 230000002452 interceptive effect Effects 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- UTOMICFLROGMAE-UHFFFAOYSA-N quinoline-3,4-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CN=C21 UTOMICFLROGMAE-UHFFFAOYSA-N 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000012346 acetyl chloride Substances 0.000 description 6
- 150000001414 amino alcohols Chemical class 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000001805 chlorine compounds Chemical class 0.000 description 6
- 238000010511 deprotection reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 210000000265 leukocyte Anatomy 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
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- KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 229960002109 tuberculosis vaccine Drugs 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 201000008297 typhoid fever Diseases 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 230000037314 wound repair Effects 0.000 description 1
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
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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- 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
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- 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
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- 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
- A61P31/14—Antivirals for RNA viruses
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- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
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- 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
- A61P37/08—Antiallergic agents
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- 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
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US64044004P | 2004-12-30 | 2004-12-30 | |
| US60/640,440 | 2004-12-30 | ||
| US69725605P | 2005-07-07 | 2005-07-07 | |
| US60/697,256 | 2005-07-07 | ||
| PCT/US2005/047297 WO2006083440A2 (en) | 2004-12-30 | 2005-12-29 | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
Publications (2)
| Publication Number | Publication Date |
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| CA2594674A1 CA2594674A1 (en) | 2006-08-10 |
| CA2594674C true CA2594674C (en) | 2016-05-17 |
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| CA2594674A Expired - Fee Related CA2594674C (en) | 2004-12-30 | 2005-12-29 | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
Country Status (7)
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| US (2) | US8034938B2 (enExample) |
| EP (1) | EP1831221B1 (enExample) |
| JP (1) | JP5313502B2 (enExample) |
| AU (1) | AU2005326708C1 (enExample) |
| CA (1) | CA2594674C (enExample) |
| ES (1) | ES2392648T3 (enExample) |
| WO (1) | WO2006083440A2 (enExample) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| EP1851224A2 (en) * | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
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| AU2006232375A1 (en) | 2005-04-01 | 2006-10-12 | 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 |
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| US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
| US8507507B2 (en) | 2009-10-22 | 2013-08-13 | Gilead Sciences, Inc. | Modulators of toll-like receptors |
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| MX355623B (es) | 2011-06-03 | 2018-04-25 | 3M Innovative Properties Co | Hidrazino-1h-imidazoquinolin-4-aminas y conjugados elaborados a partir de las mismas. |
| MX347240B (es) | 2011-06-03 | 2017-04-20 | 3M Innovative Properties Co | Ligadores heterobifuncionales con segmentos polietilenglicol y conjugados modificadores de la respuesta inmunitaria elaborados a partir de los mismos. |
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| US10526309B2 (en) | 2015-10-02 | 2020-01-07 | The University Of North Carolina At Chapel Hill | Pan-TAM inhibitors and Mer/Axl dual inhibitors |
| EP3504215B1 (en) * | 2016-08-26 | 2022-04-06 | 3M Innovative Properties Company | Fused [1,2]imidazo[4,5-c]ring compounds substituted with guanidino groups |
| 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 |
| WO2019166946A1 (en) | 2018-02-28 | 2019-09-06 | Pfizer Inc. | Il-15 variants and uses thereof |
| TWI803637B (zh) | 2018-05-23 | 2023-06-01 | 美商輝瑞大藥廠 | 特異性針對gucy2c之抗體及其用途 |
| EP3797121B1 (en) | 2018-05-23 | 2024-06-19 | Pfizer Inc. | Antibodies specific for cd3 and uses thereof |
| WO2020109898A1 (en) | 2018-11-26 | 2020-06-04 | 3M Innovative Properties Company | N-1 branched alkyl ether substituted imidazo[4,5-c]quinoline compounds, compositions, and methods |
| US20220370606A1 (en) | 2018-12-21 | 2022-11-24 | Pfizer Inc. | Combination Treatments Of Cancer Comprising A TLR Agonist |
| KR20220114049A (ko) | 2019-12-17 | 2022-08-17 | 화이자 인코포레이티드 | Cd47, pd-l1에 특이적인 항체, 및 그의 용도 |
| IL299939A (en) | 2020-07-17 | 2023-03-01 | Pfizer | Therapeutic antibodies and their uses |
| WO2025104289A1 (en) | 2023-11-17 | 2025-05-22 | Medincell S.A. | Antineoplastic combinations |
Family Cites Families (339)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3314941A (en) | 1964-06-23 | 1967-04-18 | American Cyanamid Co | Novel substituted pyridodiazepins |
| DE1645976A1 (de) | 1966-06-18 | 1971-01-21 | Ajinomoto Kk | Verfahren zur Herstellung von Adenosin und 2',3'-O-Isopropylidenadenosin |
| ZA704419B (en) | 1969-07-21 | 1971-04-28 | Ici Australia Ltd | Injectable aqueous solutions of tetramisole |
| US3692907A (en) | 1970-10-27 | 1972-09-19 | Richardson Merrell Inc | Treating viral infections with bis-basic ethers and thioethers of fluorenone and fluorene and pharmaceutical compositons of the same |
| US3917624A (en) | 1972-09-27 | 1975-11-04 | Pfizer | Process for producing 2-amino-nicotinonitrile intermediates |
| US4006237A (en) | 1973-10-11 | 1977-02-01 | Beecham Group Limited | Tetrahydrocarbostyril derivatives for the prophylaxis of asthma, hayfever and rhinitis |
| US3891660A (en) | 1974-02-07 | 1975-06-24 | Squibb & Sons Inc | Derivatives of 1H-imidazo{8 4,5-c{9 pyridine-7-carboxylic acids and esters |
| US3899508A (en) | 1974-04-12 | 1975-08-12 | Lilly Co Eli | 5-(2-Aminophenyl)pyrazole-3-carboxylic acids and esters thereof |
| DE2423389A1 (de) | 1974-05-14 | 1975-12-04 | Hoechst Ag | Arzneimittel mit psychotroper wirkung und verfahren zu ihrer herstellung |
| JPS6016438B2 (ja) | 1976-10-14 | 1985-04-25 | ウェルファイド株式会社 | イミダゾキノリン誘導体 |
| US4381344A (en) | 1980-04-25 | 1983-04-26 | Burroughs Wellcome Co. | Process for producing deoxyribosides using bacterial phosphorylase |
| DE3204126A1 (de) | 1982-02-06 | 1983-08-11 | Bayer Ag, 5090 Leverkusen | Pyrazoloxazine, -thiazine, -chinoline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4758574A (en) | 1982-05-03 | 1988-07-19 | Eli Lilly And Company | 2-phenylimidazio (4,5-c) pyridines |
| US4563525A (en) | 1983-05-31 | 1986-01-07 | Ici Americas Inc. | Process for preparing pyrazolopyridine compounds |
| CA1271477A (en) | 1983-11-18 | 1990-07-10 | John F. Gerster | 1h-imidazo[4,5-c]quinolin-4-amines |
| 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 |
| 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 |
| JPS61112075A (ja) | 1984-11-05 | 1986-05-30 | Shionogi & Co Ltd | チエニルピラゾロキノリン誘導体 |
| US4593821A (en) | 1985-04-25 | 1986-06-10 | Laros Equipment Company, Inc. | Belt separator for blow molding parts |
| US4668686A (en) | 1985-04-25 | 1987-05-26 | Bristol-Myers Company | Imidazoquinoline antithrombrogenic cardiotonic agents |
| US4698346A (en) | 1985-05-08 | 1987-10-06 | Usv Pharmaceutical Corporation | Thiazolo[5,4-h]quinoline compounds useful as anti-allergy agents |
| US4826830A (en) | 1985-07-31 | 1989-05-02 | Jui Han | Topical application of glyciphosphoramide |
| CA1306260C (en) | 1985-10-18 | 1992-08-11 | Shionogi & Co., Ltd. | Condensed imidazopyridine derivatives |
| HU197019B (en) | 1985-11-12 | 1989-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing thiqzolo (4,5-c) quinoline derivatives and pharmaceuticals comprising same |
| US4837378A (en) | 1986-01-15 | 1989-06-06 | Curatek Pharmaceuticals, Inc. | Topical metronidazole formulations and therapeutic uses thereof |
| JPS6310787A (ja) | 1986-03-06 | 1988-01-18 | Takeda Chem Ind Ltd | ヌクレオシド類縁体、その製造法および抗ウイルス剤 |
| US4775674A (en) | 1986-05-23 | 1988-10-04 | Bristol-Myers Company | Imidazoquinolinylether derivatives useful as phosphodiesterase and blood aggregation inhibitors |
| CA1287061C (en) | 1986-06-27 | 1991-07-30 | Roche Holding Ltd. | Pyridine ethanolamine derivatives |
| US5500228A (en) | 1987-05-26 | 1996-03-19 | American Cyanamid Company | Phase separation-microencapsulated pharmaceuticals compositions useful for alleviating dental disease |
| US4880779A (en) | 1987-07-31 | 1989-11-14 | Research Corporation Technologies, Inc. | Method of prevention or treatment of AIDS by inhibition of human immunodeficiency virus |
| US4774339A (en) | 1987-08-10 | 1988-09-27 | Molecular Probes, Inc. | Chemically reactive dipyrrometheneboron difluoride dyes |
| JPH01180156A (ja) | 1988-01-12 | 1989-07-18 | Nec Corp | パケットスイッチング回路 |
| US5536743A (en) | 1988-01-15 | 1996-07-16 | Curatek Pharmaceuticals Limited Partnership | Intravaginal treatment of vaginal infections with buffered metronidazole compositions |
| US5225183A (en) | 1988-12-06 | 1993-07-06 | Riker Laboratories, Inc. | Medicinal aerosol formulations |
| 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 |
| US5736553A (en) | 1988-12-15 | 1998-04-07 | 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 |
| US5457183A (en) | 1989-03-06 | 1995-10-10 | Board Of Regents, The University Of Texas System | Hydroxylated texaphyrins |
| US5037986A (en) | 1989-03-23 | 1991-08-06 | Minnesota Mining And Manufacturing Company | Olefinic 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 |
| 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 |
| US5750134A (en) | 1989-11-03 | 1998-05-12 | Riker Laboratories, Inc. | Bioadhesive composition and patch |
| JPH05503517A (ja) | 1989-12-18 | 1993-06-10 | バージニア・コモンウェルス・ユニバーシティ | シグマレセプターリガンド及びその用途 |
| US5274113A (en) | 1991-11-01 | 1993-12-28 | Molecular Probes, Inc. | Long wavelength chemically reactive dipyrrometheneboron difluoride dyes and conjugates |
| BR9106391A (pt) | 1990-04-30 | 1993-04-27 | Isis Pharmaceuticals Inc | Oligonucleotideo ou analogo de oligonucleotideo,processo para modular o metaboslismo do acido araquidonico em um animal,e,processo para tratar um anumal suspeito de ter uma doenca que e modulada por mudancas na sintese ou no metabolismo do acido arquidonico |
| EP0461040A1 (fr) | 1990-06-08 | 1991-12-11 | Roussel Uclaf | Dérivés de l'imidazole, leur procédé de préparation, les intermédiaires obtenus, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant |
| JP2660086B2 (ja) | 1990-07-03 | 1997-10-08 | 明治製菓株式会社 | 脳及び心機能障害改善剤 |
| CA2093132C (en) | 1990-10-05 | 2002-02-26 | John F. Gerster | Process for the preparation of imidazo[4,5-c]quinolin-4-amines |
| MX9203481A (es) | 1990-10-18 | 1992-07-01 | Minnesota Mining & Mfg | Formulaciones. |
| US5248782A (en) | 1990-12-18 | 1993-09-28 | Molecular Probes, Inc. | Long wavelength heteroaryl-substituted dipyrrometheneboron difluoride dyes |
| 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 |
| 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 |
| JPH04327587A (ja) | 1991-04-26 | 1992-11-17 | Asahi Chem Ind Co Ltd | ６’−ｃ−アルキル−３−デアザネプラノシンａ誘導体、その製造法およびその用途 |
| US5187288A (en) | 1991-05-22 | 1993-02-16 | Molecular Probes, Inc. | Ethenyl-substituted dipyrrometheneboron difluoride dyes and their synthesis |
| US5268376A (en) | 1991-09-04 | 1993-12-07 | Minnesota Mining And Manufacturing Company | 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| TW300219B (enExample) | 1991-09-14 | 1997-03-11 | Hoechst Ag | |
| PH31245A (en) | 1991-10-30 | 1998-06-18 | Janssen Pharmaceutica Nv | 1,3-Dihydro-2H-imidazoÄ4,5-BÜ-quinolin-2-one derivatives. |
| US5266575A (en) | 1991-11-06 | 1993-11-30 | Minnesota Mining And Manufacturing Company | 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines |
| US5378848A (en) | 1992-02-12 | 1995-01-03 | Shionogi & Co., Ltd. | Condensed imidazopyridine derivatives |
| IL105325A (en) | 1992-04-16 | 1996-11-14 | Minnesota Mining & Mfg | Immunogen/vaccine adjuvant composition |
| ATE155681T1 (de) | 1992-05-18 | 1997-08-15 | Minnesota Mining & Mfg | Einrichtung zur transmucosalen wirkstoffabgabe |
| US5352680A (en) | 1992-07-15 | 1994-10-04 | Regents Of The University Of Minnesota | Delta opioid receptor antagonists to block opioid agonist tolerance and dependence |
| 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 |
| US5395937A (en) | 1993-01-29 | 1995-03-07 | Minnesota Mining And Manufacturing Company | Process for preparing quinoline amines |
| CA2156408C (en) | 1993-03-17 | 2005-02-15 | Daniel C. Duan | Aerosol formulation containing a polyester dispersing aid |
| DE4309969A1 (de) | 1993-03-26 | 1994-09-29 | Bayer Ag | Substituierte heteroanellierte Imidazole |
| DE69314318T2 (de) | 1993-04-27 | 1998-04-09 | Agfa Gevaert Nv | Verfahren zum Einfügen von einer Wasserumlöslichen Verbindung in eine hydrophile Schicht |
| US5352784A (en) | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| ES2149276T3 (es) | 1993-07-15 | 2000-11-01 | Minnesota Mining & Mfg | Imidazo(4,5-c)piridin-4-aminas. |
| US5648516A (en) | 1994-07-20 | 1997-07-15 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| CA2131680C (en) | 1993-09-17 | 2006-11-07 | Gerhard Stucky | Process for preparing imidazopyridine derivatives |
| US5837809A (en) | 1995-08-11 | 1998-11-17 | Oregon Health Sciences University | Mammalian opioid receptor ligand and uses |
| JPH07163368A (ja) | 1993-12-15 | 1995-06-27 | Hayashibara Biochem Lab Inc | 組換えｄｎａとその組換えｄｎａを含む形質転換体 |
| TW574214B (en) | 1994-06-08 | 2004-02-01 | Pfizer | Corticotropin releasing factor antagonists |
| DE69535036T3 (de) | 1994-07-15 | 2011-07-07 | The University of Iowa Research Foundation, IA | Immunomodulatorische oligonukleotide |
| US6239116B1 (en) | 1994-07-15 | 2001-05-29 | University Of Iowa Research Foundation | Immunostimulatory nucleic acid molecules |
| US6207646B1 (en) | 1994-07-15 | 2001-03-27 | University Of Iowa Research Foundation | Immunostimulatory nucleic acid molecules |
| US5612377A (en) | 1994-08-04 | 1997-03-18 | Minnesota Mining And Manufacturing Company | Method of inhibiting leukotriene biosynthesis |
| US5644063A (en) | 1994-09-08 | 1997-07-01 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]pyridin-4-amine intermediates |
| GB9420168D0 (en) | 1994-10-06 | 1994-11-23 | Boots Co Plc | Therapeutic agents |
| US5571819A (en) | 1994-11-22 | 1996-11-05 | Sabb; Annmarie L. | Imidazopyridines as muscarinic agents |
| US5482936A (en) * | 1995-01-12 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-C]quinoline amines |
| US6071949A (en) | 1995-03-14 | 2000-06-06 | The United States Of America As Represented By The Department Of Health And Human Services | Use of lipoxygenase inhibitors as anti-cancer therapeutic and intervention agents |
| US5585612A (en) | 1995-03-20 | 1996-12-17 | Harp Enterprises, Inc. | Method and apparatus for voting |
| FR2732605B1 (fr) | 1995-04-07 | 1997-05-16 | Pasteur Merieux Serums Vacc | Composition destinee a l'induction d'une reponse immunitaire mucosale |
| US5766789A (en) | 1995-09-29 | 1998-06-16 | Energetics Systems Corporation | Electrical energy devices |
| DK0778277T3 (da) | 1995-12-08 | 2003-10-27 | Pfizer | Substituerede heterocycliske derivater som CRF antagonister |
| 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 |
| US5939047A (en) | 1996-04-16 | 1999-08-17 | Jernberg; Gary R. | Local delivery of chemotherapeutic agents for treatment of periodontal disease |
| US5861268A (en) | 1996-05-23 | 1999-01-19 | Biomide Investment Limited Partnership | Method for induction of tumor cell apoptosis with chemical inhibitors targeted to 12-lipoxygenase |
| 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 |
| ATE283855T1 (de) | 1996-07-03 | 2004-12-15 | Sumitomo Pharma | Neue purinderivate |
| US6387938B1 (en) | 1996-07-05 | 2002-05-14 | Mochida Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| HUP9904665A3 (en) | 1996-10-25 | 2000-11-28 | Minnesota Mining And Mfg Co Sa | 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 |
| US6406705B1 (en) | 1997-03-10 | 2002-06-18 | University Of Iowa Research Foundation | Use of nucleic acids containing unmethylated CpG dinucleotide as an adjuvant |
| US6426334B1 (en) | 1997-04-30 | 2002-07-30 | Hybridon, Inc. | Oligonucleotide mediated specific cytokine induction and reduction of tumor growth in a mammal |
| US6113918A (en) | 1997-05-08 | 2000-09-05 | Ribi Immunochem Research, Inc. | Aminoalkyl glucosamine phosphate compounds and their use as adjuvants and immunoeffectors |
| US6303347B1 (en) | 1997-05-08 | 2001-10-16 | Corixa Corporation | Aminoalkyl glucosaminide phosphate compounds and their use as adjuvants and immunoeffectors |
| EP1003531B1 (en) | 1997-05-20 | 2007-08-22 | Ottawa Health Research Institute | Processes for preparing nucleic acid constructs |
| US6123957A (en) | 1997-07-16 | 2000-09-26 | Jernberg; Gary R. | Delivery of agents and method for regeneration of periodontal tissues |
| KR100528112B1 (ko) | 1997-08-20 | 2006-03-17 | 소니 가부시끼 가이샤 | 원반형 기록 매체의 제조 장치 및 방법 |
| US6309623B1 (en) | 1997-09-29 | 2001-10-30 | Inhale Therapeutic Systems, Inc. | Stabilized preparations for use in metered dose inhalers |
| CA2311742C (en) | 1997-11-28 | 2009-06-16 | Sumitomo Pharmaceuticals Co., Ltd. | 6-amino-9-benzyl-8-hydroxypurine derivatives |
| US6121323A (en) | 1997-12-03 | 2000-09-19 | 3M Innovative Properties Company | Bishydroxyureas |
| 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 |
| TW572758B (en) | 1997-12-22 | 2004-01-21 | Sumitomo Pharma | Type 2 helper T cell-selective immune response inhibitors comprising purine derivatives |
| 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 |
| US6114058A (en) | 1998-05-26 | 2000-09-05 | Siemens Westinghouse Power Corporation | Iron aluminide alloy container for solid oxide fuel cells |
| 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 |
| US5962636A (en) | 1998-08-12 | 1999-10-05 | Amgen Canada Inc. | Peptides capable of modulating inflammatory heart disease |
| JP2000119271A (ja) | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | １ｈ―イミダゾピリジン誘導体 |
| US6518280B2 (en) | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
| NZ512628A (en) | 1999-01-08 | 2004-03-26 | 3M Innovative Properties Co | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| EP1495758A3 (en) | 1999-01-08 | 2005-04-13 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| 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 |
| 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 |
| US6294271B1 (en) | 1999-02-12 | 2001-09-25 | Shin-Etsu Chemical Co., Ltd. | Flip-chip type semiconductor device sealing material and flip-chip type semiconductor device |
| 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 |
| EP1171609B1 (en) | 1999-04-12 | 2008-06-25 | Lexicon Pharmaceuticals, Inc. | Lipoxygenase proteins and polynucleotides encoding the same |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6331539B1 (en) | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide 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 |
| US6315985B1 (en) | 1999-06-18 | 2001-11-13 | 3M Innovative Properties Company | C-17/21 OH 20-ketosteroid solution aerosol products with enhanced chemical stability |
| ES2233426T3 (es) | 1999-08-13 | 2005-06-16 | Hybridon, Inc. | Modulacion de la estimulacion inmunitaria medida por cpg de oligonucleotido por modificacion de la posicion de los nucleosidos. |
| US6432989B1 (en) | 1999-08-27 | 2002-08-13 | Pfizer Inc | Use of CRF antagonists to treat circadian rhythm disorders |
| CO5271670A1 (es) | 1999-10-29 | 2003-04-30 | Pfizer Prod Inc | Antagonistas del factor de liberacion de corticitropina y composiciones relacionadas |
| EP1666028B1 (en) | 1999-10-29 | 2010-03-24 | Novartis AG | Dry powder compositions having improved dispersivity |
| 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 |
| US6313156B1 (en) | 1999-12-23 | 2001-11-06 | Icos Corporation | Thiazole compounds as cyclic-AMP-specific phosphodiesterase inhibitors |
| US20040023870A1 (en) | 2000-01-21 | 2004-02-05 | Douglas Dedera | Methods of therapy and diagnosis using targeting of cells that express toll-like receptor proteins |
| GB0001704D0 (en) | 2000-01-25 | 2000-03-15 | Glaxo Group Ltd | Protein |
| KR20020073211A (ko) | 2000-02-09 | 2002-09-19 | 호쿠리쿠 세이야쿠 가부시키가이샤 | 1 에이치-이미다조피리딘유도체 |
| WO2001070663A2 (en) | 2000-03-17 | 2001-09-27 | Corixa Corporation | Novel amphipathic aldehydes and their use as adjuvants and immunoeffectors |
| US20010046968A1 (en) | 2000-03-23 | 2001-11-29 | Zagon Ian S. | Opioid growth factor modulates angiogenesis |
| EP1270578A4 (en) | 2000-03-30 | 2004-11-03 | Shionogi & Co | NOVEL PROCESS FOR PRODUCING MOLTEN IMIDAZOPYRIDINE DERIVATIVE AND NOVEL CRYSTALLINE FORM |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| US20020137101A1 (en) | 2000-05-19 | 2002-09-26 | Meyers Rachel A. | 46638, a novel human lipoxygenase family member and uses thereof |
| DE10020465A1 (de) | 2000-04-26 | 2001-11-08 | Osram Opto Semiconductors Gmbh | Strahlungsemittierendes Halbleiterbauelement mit Lumineszenzkonversionselement |
| DE10029580C1 (de) | 2000-06-15 | 2002-01-10 | Ferton Holding Sa | Vorrichtung zum Entfernen von Körpersteinen mit einem intrakorporalen Lithotripter |
| US6387383B1 (en) | 2000-08-03 | 2002-05-14 | Dow Pharmaceutical Sciences | Topical low-viscosity gel composition |
| US6900016B1 (en) | 2000-09-08 | 2005-05-31 | Applera Corporation | Polymorphisms in known genes associated with inflammatory autoimmune disease, methods of detection and uses thereof |
| US20020055517A1 (en) | 2000-09-15 | 2002-05-09 | 3M Innovative Properties Company | Methods for delaying recurrence of herpes virus symptoms |
| WO2002022809A2 (en) | 2000-09-15 | 2002-03-21 | Coley Pharmaceutical Gmbh | PROCESS FOR HIGH THROUGHPUT SCREENING OF CpG-BASED IMMUNO-AGONIST/ANTAGONIST |
| GB0023008D0 (en) | 2000-09-20 | 2000-11-01 | Glaxo Group Ltd | Improvements in vaccination |
| WO2002046479A1 (fr) | 2000-12-07 | 2002-06-13 | Aoyama Seisakusho Co., Ltd. | Procede de cuisson d'element d'acier |
| US6677347B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| US20020110840A1 (en) | 2000-12-08 | 2002-08-15 | 3M Innovative Properties Company | Screening method for identifying compounds that selectively induce interferon alpha |
| US6677348B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| US6664264B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US20060142202A1 (en) | 2000-12-08 | 2006-06-29 | 3M Innovative Properties Company | Compositions and methods for targeted delivery of immune response modifiers |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| UA75622C2 (en) | 2000-12-08 | 2006-05-15 | 3M Innovative Properties Co | Aryl ether substituted imidazoquinolines, pharmaceutical composition based thereon |
| US6667312B2 (en) | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6660735B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| US6664260B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Heterocyclic ether substituted imidazoquinolines |
| US6664265B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| UA74593C2 (en) | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
| US20020107262A1 (en) | 2000-12-08 | 2002-08-08 | 3M Innovative Properties Company | Substituted imidazopyridines |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| US6660747B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| KR100455713B1 (ko) | 2001-01-29 | 2004-11-06 | 호남석유화학 주식회사 | 올레핀 중합용 다중핵 메탈로센 촉매 및 이를 이용한중합방법 |
| US20020182274A1 (en) | 2001-03-21 | 2002-12-05 | Kung-Ming Lu | Methods for inhibiting cancer growth, reducing infection and promoting general health with a fermented soy extract |
| DE60228229D1 (de) | 2001-04-17 | 2008-09-25 | Dainippon Sumitomo Pharma Co | Neue adeninderivate |
| ATE463505T1 (de) | 2001-04-20 | 2010-04-15 | Inst Systems Biology | Toll-ähnlichen-rezeptor-5-liganden und verwendungsverfahren |
| US20020193729A1 (en) | 2001-04-20 | 2002-12-19 | Cormier Michel J.N. | Microprojection array immunization patch and method |
| US6627639B2 (en) | 2001-04-26 | 2003-09-30 | Wyeth | Uses for indoletetrahydropyridine derivatives of 2,3-dihydro-7H-[1,4]dioxino-[2,3-e]indole |
| US7226928B2 (en) | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
| US6756399B2 (en) | 2001-06-29 | 2004-06-29 | The United States Of America As Represented By The Department Of Health And Human Services | Use of lipoxygenase inhibitors and PPAR ligands as anti-cancer therapeutic and intervention agents |
| CN1250550C (zh) | 2001-07-16 | 2006-04-12 | 盐野义制药株式会社 | 脒衍生物的制备方法 |
| WO2003020889A2 (en) | 2001-08-30 | 2003-03-13 | 3M Innovative Properties Company | Methods of maturing plasmacytoid dendritic cells using immune response modifier molecules |
| WO2003030902A1 (en) | 2001-10-09 | 2003-04-17 | Tularik Inc. | Imidazole derivates as anti-inflammatory agents |
| US20030139364A1 (en) | 2001-10-12 | 2003-07-24 | University Of Iowa Research Foundation | Methods and products for enhancing immune responses using imidazoquinoline compounds |
| EP1719511B1 (en) | 2001-11-16 | 2008-12-10 | 3M Innovative Properties Company | N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide, a pharmaceutical composition comprising the same and use thereof |
| US20050009858A1 (en) | 2001-11-17 | 2005-01-13 | Martinez-Colon Maria I | Imiquimod therapies |
| GEP20074099B (en) | 2001-11-27 | 2007-05-10 | Anadys Pharmaceuticals Inc | 3-β-D-RIBOFURANO-SYLTHIAZOLO[4,5-d]PYRIDIMINE NUCLEOSIDES AND USES THEREOF |
| DK1450804T3 (da) | 2001-11-29 | 2009-01-05 | 3M Innovative Properties Co | Farmaceutiske formulelringer, der omfatter et immunsvarmodificerende middel |
| US6677349B1 (en) | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6775514B2 (en) | 2002-01-11 | 2004-08-10 | Xerox Corporation | Substrate size monitoring system for use in copier/printers |
| US6525028B1 (en) | 2002-02-04 | 2003-02-25 | Corixa Corporation | Immunoeffector compounds |
| US20050281813A1 (en) | 2002-02-14 | 2005-12-22 | Nuvelo, Inc. | Methods of therapy and diagnosis using targeting of cells that express toll-like receptor proteins |
| EP1478327B1 (en) | 2002-02-22 | 2015-04-29 | Meda AB | Method of reducing and treating uvb-induced immunosuppression |
| US20030185835A1 (en) | 2002-03-19 | 2003-10-02 | Braun Ralph P. | Adjuvant for vaccines |
| ATE491471T1 (de) | 2002-03-19 | 2011-01-15 | Powderject Res Ltd | Adjuvantien für dns impstoffe basierend auf imidazochinoline |
| RU2302865C2 (ru) | 2002-04-04 | 2007-07-20 | Коли Фармасьютикал Гмбх | Иммуностимулирующие g, u-содержащие олигорибонуклеотиды |
| CA2484192C (en) | 2002-04-30 | 2012-10-02 | Unigen Pharmaceuticals, Inc. | Formulation of a mixture of free-b-ring flavonoids and flavans as a therapeutic agent |
| GB0211649D0 (en) | 2002-05-21 | 2002-07-03 | Novartis Ag | Organic compounds |
| WO2003101949A2 (en) | 2002-05-29 | 2003-12-11 | 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 |
| JP2005537287A (ja) | 2002-07-26 | 2005-12-08 | テバ ジョジセルジャール レースベニュタールシャシャーグ | 新規１Ｈ−イミダゾ［４，５−ｃ］キノリン−４−シアノ及び１Ｈ−イミダゾ［４，５−ｃ］キノリン−４−カルボキサミド中間体による１Ｈ−イミダゾ［４，５−ｃ］キノリン−４−アミン類の製造 |
| ATE488246T1 (de) | 2002-08-15 | 2010-12-15 | 3M Innovative Properties Co | Immunstimulatorische zusammensetzungen und verfahren zur stimulierung einer immunantwort |
| EP1542688A4 (en) | 2002-09-26 | 2010-06-02 | 3M Innovative Properties Co | 1H-imidazo dimers |
| US7199119B2 (en) | 2002-10-31 | 2007-04-03 | Amgen Inc. | Antiinflammation agents |
| WO2004043913A2 (en) | 2002-11-08 | 2004-05-27 | Trimeris, Inc. | Hetero-substituted benzimidazole compounds and antiviral uses thereof |
| AU2003287324A1 (en) | 2002-12-11 | 2004-06-30 | 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 |
| US7091214B2 (en) | 2002-12-20 | 2006-08-15 | 3M Innovative Properties Co. | Aryl substituted Imidazoquinolines |
| EP1578419A4 (en) | 2002-12-30 | 2008-11-12 | 3M Innovative Properties Co | IMMUNOSTIMULATING COMBINATIONS |
| US7375180B2 (en) | 2003-02-13 | 2008-05-20 | 3M Innovative Properties Company | Methods and compositions related to IRM compounds and Toll-like receptor 8 |
| EP1599726A4 (en) | 2003-02-27 | 2009-07-22 | 3M Innovative Properties Co | SELECTIVE MODULATION OF TLR-MEDIATED BIOLOGICAL ACTIVITY |
| WO2004078138A2 (en) | 2003-03-04 | 2004-09-16 | 3M Innovative Properties Company | Prophylactic treatment of uv-induced epidermal neoplasia |
| US7163947B2 (en) | 2003-03-07 | 2007-01-16 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
| US20040176367A1 (en) | 2003-03-07 | 2004-09-09 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
| AU2004220466A1 (en) | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Methods for diagnosing skin lesions |
| US7179253B2 (en) | 2003-03-13 | 2007-02-20 | 3M Innovative Properties Company | Method of tattoo removal |
| BRPI0408476A (pt) | 2003-03-13 | 2006-04-04 | 3M Innovative Properties Co | métodos para melhorar a qualidade da pele |
| US20040192585A1 (en) | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
| EP1613956A2 (en) | 2003-03-25 | 2006-01-11 | 3M Innovative Properties Company | Selective activation of cellular activities mediated through a common toll-like receptor |
| US7893096B2 (en) | 2003-03-28 | 2011-02-22 | Novartis Vaccines And Diagnostics, Inc. | Use of small molecule compounds for immunopotentiation |
| WO2004108072A2 (en) | 2003-04-10 | 2004-12-16 | 3M Innovative Properties Company | Delivery of immune response modifier compounds using metal-containing particulate support materials |
| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| US20040214851A1 (en) | 2003-04-28 | 2004-10-28 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
| US7731967B2 (en) | 2003-04-30 | 2010-06-08 | Novartis Vaccines And Diagnostics, Inc. | Compositions for inducing immune responses |
| US20050032829A1 (en) | 2003-06-06 | 2005-02-10 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| US6943255B2 (en) | 2003-06-06 | 2005-09-13 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| EA200600069A1 (ru) | 2003-06-20 | 2006-08-25 | Коли Фармасьютикал Гмбх | Низкомолекулярные антагонисты toll-подобных рецепторов (tlr) |
| MY157827A (en) | 2003-06-27 | 2016-07-29 | 3M Innovative Properties Co | Sulfonamide substituted imidazoquinolines |
| US20050106300A1 (en) | 2003-06-30 | 2005-05-19 | Purdue Research Foundation | Method for producing a material having an increased solubility in alcohol |
| BRPI0413143A (pt) | 2003-07-31 | 2006-10-03 | 3M Innovative Properties Co | composições para encapsulação e liberação controlada |
| US20050070460A1 (en) | 2003-08-05 | 2005-03-31 | 3M Innovative Properties Company | Infection prophylaxis using immune response modifier compounds |
| AU2004266658A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| PL1653959T3 (pl) | 2003-08-14 | 2015-10-30 | 3M Innovative Properties Co | Modyfikatory odpowiedzi immunologicznej modyfikowane lipidami |
| JP2007503268A (ja) | 2003-08-25 | 2007-02-22 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答修飾化合物の送達 |
| AU2004266162A1 (en) | 2003-08-25 | 2005-03-03 | 3M Innovative Properties Company | Immunostimulatory combinations and treatments |
| US7897597B2 (en) | 2003-08-27 | 2011-03-01 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| AU2004268665A1 (en) | 2003-09-02 | 2005-03-10 | 3M Innovative Properties Company | Methods related to the treatment of mucosal associated conditions |
| WO2005025583A2 (en) | 2003-09-05 | 2005-03-24 | Anadys Pharmaceuticals, Inc. | Tlr7 ligands for the treatment of hepatitis c |
| JP2007504269A (ja) | 2003-09-05 | 2007-03-01 | スリーエム イノベイティブ プロパティズ カンパニー | Ｃｄ５＋ｂ細胞リンパ腫の治療方法 |
| GB0321615D0 (en) | 2003-09-15 | 2003-10-15 | Glaxo Group Ltd | Improvements in vaccination |
| WO2005029037A2 (en) | 2003-09-17 | 2005-03-31 | 3M Innovative Properties Company | Selective modulation of tlr gene expression |
| 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 |
| US20090075980A1 (en) | 2003-10-03 | 2009-03-19 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and Analogs Thereof |
| US8871782B2 (en) | 2003-10-03 | 2014-10-28 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| AU2004315876B2 (en) | 2003-10-03 | 2011-05-26 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| WO2005041891A2 (en) | 2003-10-31 | 2005-05-12 | 3M Innovative Properties Company | Neutrophil activation by immune response modifier compounds |
| US20050239733A1 (en) | 2003-10-31 | 2005-10-27 | Coley Pharmaceutical Gmbh | Sequence requirements for inhibitory oligonucleotides |
| ITMI20032121A1 (it) | 2003-11-04 | 2005-05-05 | Dinamite Dipharma Spa In Forma Abbr Eviata Dipharm | Procedimento per la preparazione di imiquimod e suoi intermedi |
| AU2004291101A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
| EP1682544A4 (en) | 2003-11-14 | 2009-05-06 | 3M Innovative Properties Co | HYDROXYLAMINE SUBSTITUTED IMIDAZO RING COMPOUNDS |
| CU23404A1 (es) | 2003-11-19 | 2009-08-04 | Ct Ingenieria Genetica Biotech | Polisacáridos capsulares de neisseria meningitidis como inmunopotenciadores mucosales y formulaciones resultantes |
| AR046845A1 (es) | 2003-11-21 | 2005-12-28 | Novartis Ag | Derivados de 1h-imidazo[4,5-c]quinolina para tratamiento de enfermedades dependientes de las proteino-quinasas |
| KR20060117329A (ko) | 2003-11-21 | 2006-11-16 | 노파르티스 아게 | 단백질 키나제 저해제로서의 1ｈ-이미다조퀴놀린 유도체 |
| 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 |
| EP1689361A4 (en) | 2003-12-02 | 2009-06-17 | 3M Innovative Properties Co | THERAPEUTIC COMBINATIONS AND PROCESSES WITH IRM COMPOUNDS |
| JP2007513170A (ja) | 2003-12-04 | 2007-05-24 | スリーエム イノベイティブ プロパティズ カンパニー | スルホン置換イミダゾ環エーテル |
| EP1701955A1 (en) | 2003-12-29 | 2006-09-20 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| CA2552101A1 (en) * | 2003-12-29 | 2005-07-21 | 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 |
| WO2005065678A1 (en) | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Immunomodulatory combinations |
| EP1699788A2 (en) | 2003-12-30 | 2006-09-13 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides |
| US20070167479A1 (en) | 2004-03-15 | 2007-07-19 | Busch Terri F | Immune response modifier formulations and methods |
| EP1730143A2 (en) | 2004-03-24 | 2006-12-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005110013A2 (en) | 2004-04-09 | 2005-11-24 | 3M Innovative Properties Company | Methods, compositions, and preparations for delivery of immune response modifiers |
| 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 |
| US20080015184A1 (en) | 2004-06-14 | 2008-01-17 | 3M Innovative Properties Company | Urea Substituted Imidazopyridines, Imidazoquinolines, and Imidazonaphthyridines |
| US8017779B2 (en) | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| WO2006093514A2 (en) | 2004-06-18 | 2006-09-08 | 3M Innovative Properties Company | Aryl and arylalkylenyl substituted thiazoloquinolines and thiazolonaphthyridines |
| WO2006009832A1 (en) | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| US7897609B2 (en) | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| EP1765348B1 (en) | 2004-06-18 | 2016-08-03 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| US20060045885A1 (en) | 2004-08-27 | 2006-03-02 | Kedl Ross M | Method of eliciting an immune response against HIV |
| WO2006026470A2 (en) | 2004-08-27 | 2006-03-09 | 3M Innovative Properties Company | Hiv immunostimulatory compositions |
| WO2006028962A2 (en) | 2004-09-02 | 2006-03-16 | 3M Innovative Properties Company | 1-alkoxy 1h-imidazo ring systems and methods |
| WO2006026760A2 (en) | 2004-09-02 | 2006-03-09 | 3M Innovative Properties Company | 1-amino imidazo-containing compounds and methods |
| CA2578975A1 (en) | 2004-09-02 | 2006-03-16 | 3M Innovative Properties Company | 2-amino 1h imidazo ring systems and methods |
| WO2006028451A1 (en) | 2004-09-03 | 2006-03-16 | 3M Innovative Properties Company | 1-amino 1-h-imidazoquinolines |
| US20080193468A1 (en) | 2004-09-08 | 2008-08-14 | Children's Medical Center Corporation | Method for Stimulating the Immune Response of Newborns |
| CN101056877B (zh) | 2004-09-14 | 2010-06-09 | 诺华疫苗和诊断公司 | 咪唑并喹啉化合物 |
| US20070243215A1 (en) | 2004-10-08 | 2007-10-18 | Miller Richard L | Adjuvant for Dna Vaccines |
| WO2006063072A2 (en) | 2004-12-08 | 2006-06-15 | 3M Innovative Properties Company | Immunomodulatory compositions, combinations and methods |
| JP2008523084A (ja) | 2004-12-08 | 2008-07-03 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫賦活用合剤および方法 |
| US8080560B2 (en) | 2004-12-17 | 2011-12-20 | 3M Innovative Properties Company | Immune response modifier formulations containing oleic acid and methods |
| ZA200706251B (en) | 2004-12-30 | 2008-11-26 | Coley Pharm Group Inc | Immune response modifier formulations and methods |
| US8034938B2 (en) * | 2004-12-30 | 2011-10-11 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| AU2005322898B2 (en) | 2004-12-30 | 2011-11-24 | 3M Innovative Properties Company | Chiral fused (1,2)imidazo(4,5-c) ring compounds |
| 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 |
| SI1830876T1 (sl) | 2004-12-30 | 2015-08-31 | Meda Ab | Uporaba imikvimoda za zdravljenje kožnih metastaz, ki izhajajo iz rakavega tumorja dojke |
| US20080188513A1 (en) | 2004-12-30 | 2008-08-07 | Taked Pharmaceutical Company Limited | 1-(2-Methylpropyl)-1H-Imidazo[4,5-C](1,5]Naphthyridin-4-Amine Ethanesulfonate and 1-(2-Methylpropyl)-1H-Imidazo[4,5-C](1,5]Naphthyridin-4-Amine Methanesulfonate |
| CN101160518B (zh) | 2005-02-02 | 2010-08-04 | 膜康公司 | 探测和报告气密包装中泄漏大小的仪器和方法 |
| WO2006084251A2 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| CA2597324C (en) | 2005-02-09 | 2015-06-30 | Coley Pharmaceutical Group, Inc. | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| EP1877056A2 (en) | 2005-02-09 | 2008-01-16 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazoloý4,5-c¨ring compounds and methods |
| AU2006213746A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo(4,5-c) ring compounds and methods |
| CA2597595A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Substituted fused [1,2]imidazo[4,5-c] ring compounds and methods |
| EP1845988A2 (en) | 2005-02-11 | 2007-10-24 | 3M Innovative Properties Company | Substituted imidazoquinolines and imidazonaphthyridines |
| 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 |
| EP1851220A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazonaphthyridines |
| EP1851224A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
| WO2006091647A2 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Method of preferentially inducing the biosynthesis of interferon |
| WO2006099275A2 (en) | 2005-03-14 | 2006-09-21 | 3M Innovative Properties Company | Method of treating actinic keratosis |
| WO2006107771A2 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | PYRAZOLO[3,4-c]QUINOLINES, PYRAZOLO[3,4-c]NAPHTHYRIDINES, ANALOGS THEREOF, AND METHODS |
| AU2006244635A1 (en) | 2005-04-01 | 2006-11-16 | Coley Pharmaceutical Group, Inc. | Ring closing and related methods and intermediates |
| AU2006232375A1 (en) | 2005-04-01 | 2006-10-12 | 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 |
| CA2602683A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| EP1874345B1 (en) | 2005-04-25 | 2012-08-15 | 3M Innovative Properties Company | Immunostimulatory compositions |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| CN101253173A (zh) | 2005-09-02 | 2008-08-27 | 辉瑞有限公司 | 羟基取代的1h-咪唑并吡啶和方法 |
| 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 |
| AU2006287270A1 (en) | 2005-09-09 | 2007-03-15 | Coley Pharmaceutical Group, Inc. | Amide and carbamate derivatives of N-{2-[4-amino-2- (ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide and methods |
| US8889154B2 (en) | 2005-09-15 | 2014-11-18 | Medicis Pharmaceutical Corporation | Packaging for 1-(2-methylpropyl)-1H-imidazo[4,5-c] quinolin-4-amine-containing formulation |
| WO2007035935A1 (en) | 2005-09-23 | 2007-03-29 | Coley Pharmaceutical Group, Inc. | METHOD FOR 1H-IMIDAZO[4,5-c]PYRIDINES AND ANALOGS THEREOF |
| EP1948173B1 (en) | 2005-11-04 | 2013-07-17 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1h-imidazoquinolines and methods |
| WO2007062043A1 (en) | 2005-11-23 | 2007-05-31 | Coley Pharmaceutical Group Inc. | Method of activating murine toll-like receptor 8 |
| MX2008007864A (es) | 2005-12-16 | 2009-03-04 | Coley Pharm Group Inc | Imidazoquinolinas, imidazonaftiridinas, e imidazopiridinas sustituidas, composiciones y metodos. |
| WO2007079171A2 (en) | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for hodgkin's lymphoma |
| WO2007079169A2 (en) | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for acute myeloid leukemia |
| JP2009522296A (ja) | 2005-12-28 | 2009-06-11 | スリーエム イノベイティブ プロパティズ カンパニー | 皮膚のｔ細胞リンパ腫の治療 |
| WO2007079146A1 (en) | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc | Treatment for non-hodgkin's lymphoma |
| WO2007079202A2 (en) | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for acute lymhoblastic leukemia |
| WO2007079086A1 (en) | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Pyrazoloalkyl substituted imidazo ring compounds and methods |
| US20090306388A1 (en) | 2006-02-10 | 2009-12-10 | Pfizer Inc. | Method for substituted ih-imidazo[4,5-c] pyridines |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 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 |
| WO2007106852A2 (en) | 2006-03-15 | 2007-09-20 | Coley Pharmaceutical Group, Inc. | Substituted fused[1,2]imidazo[4,5-c] ring compounds and methods |
| WO2007143526A2 (en) | 2006-06-05 | 2007-12-13 | Coley Pharmaceutical Group, Inc. | Substituted tetrahydroimidazonaphthyridines and methods |
| WO2007149802A2 (en) | 2006-06-19 | 2007-12-27 | 3M Innovative Properties Company | Formulation for delivery of immune response modifiers |
| 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 |
| WO2008014227A2 (en) * | 2006-07-24 | 2008-01-31 | Huntsman Petrochemical Corporation | Light colored foam for use in marine applications |
| WO2008016475A2 (en) | 2006-07-31 | 2008-02-07 | 3M Innovative Properties Company | Immune response modifier compositions 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 |
| WO2008036312A1 (en) | 2006-09-19 | 2008-03-27 | Coley Pharmaceutical Group, Inc. | Fungicidal methods using immune response modifier compounds |
| WO2008045543A1 (en) | 2006-10-13 | 2008-04-17 | Coley Pharmaceutical Group, Inc. | Substituted 4h-imidazo [4, 5, 1-ij] [1, 6] naphthyridine-9-amines and their pharmaceutical use |
| US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
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| US8350034B2 (en) | 2013-01-08 |
| US20110293654A1 (en) | 2011-12-01 |
| US8034938B2 (en) | 2011-10-11 |
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| AU2005326708A1 (en) | 2006-08-10 |
| ES2392648T3 (es) | 2012-12-12 |
| JP2008529974A (ja) | 2008-08-07 |
| JP5313502B2 (ja) | 2013-10-09 |
| EP1831221A4 (en) | 2008-11-05 |
| CA2594674A1 (en) | 2006-08-10 |
| WO2006083440A2 (en) | 2006-08-10 |
| EP1831221B1 (en) | 2012-08-08 |
| WO2006083440A3 (en) | 2007-06-21 |
| US20080085895A1 (en) | 2008-04-10 |
| AU2005326708B2 (en) | 2012-03-15 |
| EP1831221A2 (en) | 2007-09-12 |
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