CZ307184B6 - 2-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naftyridin-4-amin a farmaceutická kompozice s jeho obsahem - Google Patents
2-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naftyridin-4-amin a farmaceutická kompozice s jeho obsahem Download PDFInfo
- Publication number
- CZ307184B6 CZ307184B6 CZ2007-268A CZ2007268A CZ307184B6 CZ 307184 B6 CZ307184 B6 CZ 307184B6 CZ 2007268 A CZ2007268 A CZ 2007268A CZ 307184 B6 CZ307184 B6 CZ 307184B6
- Authority
- CZ
- Czechia
- Prior art keywords
- compounds
- compound
- imidazo
- formula
- methylpropyl
- Prior art date
Links
- ZXBCLVSLRUWISJ-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C3N(CC(C)C)C(C)=NC3=C(N)N=C21 ZXBCLVSLRUWISJ-UHFFFAOYSA-N 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims 2
- 102000004127 Cytokines Human genes 0.000 abstract description 27
- 108090000695 Cytokines Proteins 0.000 abstract description 27
- 108010050904 Interferons Proteins 0.000 abstract description 21
- 102000014150 Interferons Human genes 0.000 abstract description 21
- 229940079322 interferon Drugs 0.000 abstract description 19
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract description 12
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 9
- 102000003390 tumor necrosis factor Human genes 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000000840 anti-viral effect Effects 0.000 abstract description 2
- VFTLXHXYGQSOEN-UHFFFAOYSA-N 1h-imidazo[4,5-b][1,8]naphthyridine Chemical compound C1=CN=C2NC3=NC=NC3=CC2=C1 VFTLXHXYGQSOEN-UHFFFAOYSA-N 0.000 abstract 1
- ZZXQWFQBPSUCAF-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-b][1,8]naphthyridine Chemical compound N1C2=NC=CC=C2C=C2C1NCN2 ZZXQWFQBPSUCAF-UHFFFAOYSA-N 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 13
- 201000010099 disease Diseases 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 230000003612 virological effect Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- 230000006698 induction Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000028993 immune response Effects 0.000 description 8
- -1 acetic acid Chemical class 0.000 description 7
- 238000004166 bioassay Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- 210000000601 blood cell Anatomy 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000710188 Encephalomyocarditis virus Species 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 230000000120 cytopathologic effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 230000001939 inductive effect Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000009385 viral infection Effects 0.000 description 4
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 210000005260 human cell Anatomy 0.000 description 3
- 239000002955 immunomodulating agent Substances 0.000 description 3
- 229940121354 immunomodulator Drugs 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 230000001613 neoplastic effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KFAJXZVDBVRZRC-UHFFFAOYSA-N 1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(N)=CC=NC2=C1 KFAJXZVDBVRZRC-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 208000009889 Herpes Simplex Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102000006992 Interferon-alpha Human genes 0.000 description 2
- 108010047761 Interferon-alpha Proteins 0.000 description 2
- 108010002352 Interleukin-1 Proteins 0.000 description 2
- 102000000589 Interleukin-1 Human genes 0.000 description 2
- 108010063738 Interleukins Proteins 0.000 description 2
- 102000015696 Interleukins Human genes 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- 229930182816 L-glutamine Natural products 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000012980 RPMI-1640 medium Substances 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 210000003719 b-lymphocyte Anatomy 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- 229940047124 interferons Drugs 0.000 description 2
- 229940047122 interleukins Drugs 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 201000005296 lung carcinoma Diseases 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YJKZDGOMTKOYQK-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1CCC1CCNCC1 YJKZDGOMTKOYQK-UHFFFAOYSA-N 0.000 description 1
- HDDNSPWJCZZICL-UHFFFAOYSA-N 1-(6-methoxyquinolin-8-yl)-2-methylimidazo[4,5-c]quinoline Chemical compound N1=CC=CC2=CC(OC)=CC(N3C4=C5C=CC=CC5=NC=C4N=C3C)=C21 HDDNSPWJCZZICL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- KRULLMMDEYYKGQ-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C3N(CC(C)C)C(C)=NC3=CN=C21 KRULLMMDEYYKGQ-UHFFFAOYSA-N 0.000 description 1
- HFULIQZCEBYHHA-UHFFFAOYSA-N 3-nitro-1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(N)=C([N+]([O-])=O)C=NC2=C1 HFULIQZCEBYHHA-UHFFFAOYSA-N 0.000 description 1
- BPZZDZZOBAZEPJ-UHFFFAOYSA-N 3-nitro-1h-1,5-naphthyridin-4-one Chemical compound C1=CN=C2C(O)=C([N+]([O-])=O)C=NC2=C1 BPZZDZZOBAZEPJ-UHFFFAOYSA-N 0.000 description 1
- GALJZRVFTQQJLR-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,7]naphthyridine Chemical compound C1=NC=CC2=C(NC=N3)C3=CN=C21 GALJZRVFTQQJLR-UHFFFAOYSA-N 0.000 description 1
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical group C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 description 1
- NMCJKXIKZNDEMJ-UHFFFAOYSA-N 4-(2-methylpropyl)-3-nitro-3h-1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(CC(C)C)(N)C([N+]([O-])=O)C=NC2=C1 NMCJKXIKZNDEMJ-UHFFFAOYSA-N 0.000 description 1
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical class C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 1
- FDOIXMGDTOEUQL-UHFFFAOYSA-N 4-chloro-3-nitro-1,5-naphthyridine Chemical compound C1=CC=NC2=C(Cl)C([N+](=O)[O-])=CN=C21 FDOIXMGDTOEUQL-UHFFFAOYSA-N 0.000 description 1
- BSPFJSMHIAIXQW-UHFFFAOYSA-N 4-n-(2-methylpropyl)-1,5-naphthyridine-3,4-diamine Chemical compound C1=CN=C2C(NCC(C)C)=C(N)C=NC2=C1 BSPFJSMHIAIXQW-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 206010059313 Anogenital warts Diseases 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000013165 Bowen disease Diseases 0.000 description 1
- 208000019337 Bowen disease of the skin Diseases 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010008263 Cervical dysplasia Diseases 0.000 description 1
- 241000606161 Chlamydia Species 0.000 description 1
- 208000000907 Condylomata Acuminata Diseases 0.000 description 1
- 208000006081 Cryptococcal meningitis Diseases 0.000 description 1
- 208000008953 Cryptosporidiosis Diseases 0.000 description 1
- 206010011502 Cryptosporidiosis infection Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001315286 Damon Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 238000008157 ELISA kit Methods 0.000 description 1
- 206010014950 Eosinophilia Diseases 0.000 description 1
- 208000032027 Essential Thrombocythemia Diseases 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 201000002563 Histoplasmosis Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 206010027209 Meningitis cryptococcal Diseases 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 241000186367 Mycobacterium avium Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241001319148 Pharmacis Species 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 241000233870 Pneumocystis Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000024932 T cell mediated immunity Effects 0.000 description 1
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
- 201000005485 Toxoplasmosis Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000033289 adaptive immune response Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 208000025009 anogenital human papillomavirus infection Diseases 0.000 description 1
- 201000004201 anogenital venereal wart Diseases 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
- 206010006060 bowenoid papulosis Diseases 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 239000013553 cell monolayer Substances 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 208000007951 cervical intraepithelial neoplasia Diseases 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012228 culture supernatant Substances 0.000 description 1
- 201000007241 cutaneous T cell lymphoma Diseases 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000556 factor analysis Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000012997 ficoll-paque Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- NSHFLKZNBPJNPA-UHFFFAOYSA-N imidazo[4,5-c]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)N=C3C=NC2=C1 NSHFLKZNBPJNPA-UHFFFAOYSA-N 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000022023 interleukin-5 production Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- MQUIHBQDYYAEMH-UHFFFAOYSA-N methedrone Chemical compound CNC(C)C(=O)C1=CC=C(OC)C=C1 MQUIHBQDYYAEMH-UHFFFAOYSA-N 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- PEJBARJFGXOAIR-UHFFFAOYSA-N n-(2-methylpropyl)-3-nitro-1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(NCC(C)C)=C([N+]([O-])=O)C=NC2=C1 PEJBARJFGXOAIR-UHFFFAOYSA-N 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 230000029069 type 2 immune response Effects 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 239000012646 vaccine adjuvant Substances 0.000 description 1
- 229940124931 vaccine adjuvant Drugs 0.000 description 1
- 230000000007 visual effect Effects 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P17/04—Antipruritics
-
- 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
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/08—Antibacterial agents for leprosy
-
- 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
- A61P31/10—Antimycotics
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P31/20—Antivirals for DNA viruses
-
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/08—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis for Pneumocystis carinii
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- AIDS & HIV (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6927697P | 1997-12-11 | 1997-12-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ2007268A3 CZ2007268A3 (cs) | 2016-09-29 |
| CZ307184B6 true CZ307184B6 (cs) | 2018-02-28 |
Family
ID=22087889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ2007-268A CZ307184B6 (cs) | 1997-12-11 | 1998-12-11 | 2-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naftyridin-4-amin a farmaceutická kompozice s jeho obsahem |
Country Status (28)
Families Citing this family (223)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| UA67760C2 (uk) | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
| US6518280B2 (en) | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
| EP1140091B1 (en) | 1999-01-08 | 2005-09-21 | 3M Innovative Properties Company | Formulations comprising imiquimod or other immune response modifiers for treating cervical dysplasia |
| US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| 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 |
| US6558951B1 (en) * | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| SI1198233T1 (sl) * | 1999-06-10 | 2007-02-28 | 3M Innovative Properties Co | S sulfonamidom in sulfamidom substituirani imidazokinolini |
| US6451810B1 (en) * | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6331539B1 (en) | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| EP1438958A1 (en) * | 1999-06-10 | 2004-07-21 | 3M Innovative Properties Company | Carbamate substituted imidazoquinolines |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6916925B1 (en) | 1999-11-05 | 2005-07-12 | 3M Innovative Properties Co. | Dye labeled imidazoquinoline compounds |
| US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| JP3436512B2 (ja) * | 1999-12-28 | 2003-08-11 | 株式会社デンソー | アクセル装置 |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| US20040209877A1 (en) * | 2000-04-13 | 2004-10-21 | Shelby Nancy J. | Methods for augmenting immune defenses contemplating the administration of phenolic and indoleamine-like compounds for use in animals ans humans |
| UA74593C2 (en) * | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| AU2006216669A1 (en) * | 2000-12-08 | 2006-08-31 | 3M Innovative Properties Company | Compositions and methods for targeted delivery of immune response modifiers |
| US6545017B1 (en) * | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6545016B1 (en) * | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US6660747B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6677348B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| AU3249802A (en) * | 2000-12-08 | 2002-06-18 | 3M Innovative Properties Co | Screening method for identifying compounds that selectively induce interferon alpha |
| US6677347B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| UA74852C2 (en) * | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| 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 |
| US6660735B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| US7226928B2 (en) * | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
| WO2003020889A2 (en) * | 2001-08-30 | 2003-03-13 | 3M Innovative Properties Company | Methods of maturing plasmacytoid dendritic cells using immune response modifier molecules |
| US20040014779A1 (en) * | 2001-11-16 | 2004-01-22 | 3M Innovative Properties Company | Methods and compositions related to IRM compounds and toll-like recptor pathways |
| CA2467828C (en) * | 2001-11-29 | 2011-10-04 | 3M Innovative Properties Company | Pharmaceutical formulations comprising an immune response modifier |
| CA2365732A1 (en) * | 2001-12-20 | 2003-06-20 | Ibm Canada Limited-Ibm Canada Limitee | Testing measurements |
| US6677349B1 (en) * | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| SI1478327T1 (sl) * | 2002-02-22 | 2015-08-31 | Meda Ab | Metoda za zmanjšanje in zdravljenje imunosupresije, inducirane z UV-B |
| AU2003237386A1 (en) | 2002-06-07 | 2003-12-22 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| WO2004032829A2 (en) | 2002-08-15 | 2004-04-22 | 3M Innovative Properties Company | Immunostimulatory compositions and methods of stimulating an immune response |
| US6818650B2 (en) * | 2002-09-26 | 2004-11-16 | 3M Innovative Properties Company | 1H-imidazo dimers |
| AU2003287316A1 (en) * | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Assays relating to toll-like receptor activity |
| AU2003287324A1 (en) * | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Gene expression systems and recombinant cell lines |
| EP1590348A1 (en) | 2002-12-20 | 2005-11-02 | 3M Innovative Properties Company | Aryl / hetaryl substituted imidazoquinolines |
| JP2006512391A (ja) | 2002-12-30 | 2006-04-13 | スリーエム イノベイティブ プロパティズ カンパニー | 組み合わせ免疫賦活薬 |
| WO2004071459A2 (en) * | 2003-02-13 | 2004-08-26 | 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 |
| AU2004218349A1 (en) | 2003-03-04 | 2004-09-16 | 3M Innovative Properties Company | Prophylactic treatment of UV-induced epidermal neoplasia |
| CA2517655A1 (en) * | 2003-03-07 | 2004-09-23 | 3M Innovative Properties Company | 1-amino 1h-imidazoquinolines |
| US7163947B2 (en) * | 2003-03-07 | 2007-01-16 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
| US8426457B2 (en) * | 2003-03-13 | 2013-04-23 | Medicis Pharmaceutical Corporation | Methods of improving skin quality |
| US7699057B2 (en) * | 2003-03-13 | 2010-04-20 | 3M Innovative Properties Company | Methods for treating skin lesions |
| AU2004220465A1 (en) | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Method of tattoo removal |
| US20040192585A1 (en) | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
| ES2423800T3 (es) | 2003-03-28 | 2013-09-24 | Novartis Vaccines And Diagnostics, Inc. | Uso de compuestos orgánicos para la inmunopotenciación |
| AU2004244962A1 (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 |
| EP1617845A4 (en) * | 2003-04-28 | 2006-09-20 | 3M Innovative Properties Co | COMPOSITIONS AND METHODS FOR INDUCING OPOID RECEPTORS |
| US7731967B2 (en) | 2003-04-30 | 2010-06-08 | Novartis Vaccines And Diagnostics, Inc. | Compositions for inducing immune responses |
| US7176214B2 (en) | 2003-05-21 | 2007-02-13 | Bristol-Myers Squibb Company | Imidazo-fused oxazolo[4,5-β]pyridine and imidazo-fused thiazolo[4,5-β]pyridine based tricyclic compounds and pharmaceutical compositions comprising same |
| 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 |
| WO2005012488A2 (en) * | 2003-07-31 | 2005-02-10 | 3M Innovative Properties Company | Compositions for encapsulation and controlled release |
| WO2005016275A2 (en) * | 2003-08-05 | 2005-02-24 | 3M Innovative Properties Company | Formulations containing an immune response modifier |
| WO2005018556A2 (en) * | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| AU2004266657B2 (en) | 2003-08-14 | 2009-07-02 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
| JP4913593B2 (ja) * | 2003-08-14 | 2012-04-11 | スリーエム イノベイティブ プロパティズ カンパニー | 脂質修飾された免疫応答調整剤 |
| CA2551075A1 (en) * | 2003-08-25 | 2005-03-03 | 3M Innovative Properties Company | Immunostimulatory combinations and treatments |
| 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 |
| ES2406730T3 (es) | 2003-08-27 | 2013-06-07 | 3M Innovative Properties Company | Imidazoquinolinas sustituidas con ariloxi y arilalquilenoxi |
| EP1663222A4 (en) * | 2003-09-02 | 2008-05-21 | 3M Innovative Properties Co | METHODS RELATING TO THE TREATMENT OF GIANCES |
| AU2004270201A1 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for CD5+ B cell lymphoma |
| CA2536530A1 (en) | 2003-10-01 | 2005-04-14 | 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 |
| CA2540541C (en) | 2003-10-03 | 2012-03-27 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| CA2540598C (en) | 2003-10-03 | 2013-09-24 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| US7544697B2 (en) * | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| EP1680080A4 (en) * | 2003-10-31 | 2007-10-31 | 3M Innovative Properties Co | NEUTROPHILIC ACTIVATION THROUGH COMPOUNDS TO MODIFY THE IMMUNE RESPONSE |
| WO2005048945A2 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| EP1685129A4 (en) * | 2003-11-14 | 2008-10-22 | 3M Innovative Properties Co | OXIMSUBSTITUTED IMIDAZORING CONNECTIONS |
| EP1686992A4 (en) * | 2003-11-25 | 2009-11-04 | 3M Innovative Properties Co | HYDROXYLAMINE, AND IMIDAZOQUINOLEINS, AND IMIDAZOPYRIDINES AND IMIDAZONAPHTYRIDINE SUBSTITUTED WITH OXIME |
| JP4891088B2 (ja) | 2003-11-25 | 2012-03-07 | スリーエム イノベイティブ プロパティズ カンパニー | 置換されたイミダゾ環系および方法 |
| US8940755B2 (en) * | 2003-12-02 | 2015-01-27 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
| US20050226878A1 (en) * | 2003-12-02 | 2005-10-13 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
| AR048289A1 (es) * | 2003-12-04 | 2006-04-19 | 3M Innovative Properties Co | Eteres de anillos imidazo sulfona sustituidos. |
| JP2007517035A (ja) * | 2003-12-29 | 2007-06-28 | スリーエム イノベイティブ プロパティズ カンパニー | アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン |
| WO2005066172A1 (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 |
| US20050239735A1 (en) * | 2003-12-30 | 2005-10-27 | 3M Innovative Properties Company | Enhancement of immune responses |
| CA2551399A1 (en) * | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| ES2665342T3 (es) | 2004-03-15 | 2018-04-25 | Meda Ab | Formulaciones y métodos para modificadores de la respuesta inmune |
| CA2559863A1 (en) * | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| AU2005244260B2 (en) * | 2004-04-09 | 2010-08-05 | 3M Innovative Properties Company | Methods, compositions, and preparations for delivery of immune response modifiers |
| CN101426524A (zh) * | 2004-04-28 | 2009-05-06 | 3M创新有限公司 | 用于粘膜接种疫苗的组合物和方法 |
| 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 |
| WO2006038923A2 (en) * | 2004-06-18 | 2006-04-13 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| JP5128940B2 (ja) * | 2004-06-18 | 2013-01-23 | スリーエム イノベイティブ プロパティズ カンパニー | 置換イミダゾキノリン、イミダゾピリジン、およびイミダゾナフチリジン |
| WO2006009832A1 (en) * | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US7915281B2 (en) | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| US20110104186A1 (en) | 2004-06-24 | 2011-05-05 | Nicholas Valiante | Small molecule immunopotentiators and assays for their detection |
| CA2571421A1 (en) | 2004-06-24 | 2006-01-05 | Nicholas Valiante | Compounds for immunopotentiation |
| EP1786450A4 (en) * | 2004-08-27 | 2009-11-11 | 3M Innovative Properties Co | HIV IMMUNOSTIMATORY COMPOSITIONS |
| WO2006026760A2 (en) * | 2004-09-02 | 2006-03-09 | 3M Innovative Properties Company | 1-amino imidazo-containing compounds and methods |
| WO2006029115A2 (en) * | 2004-09-02 | 2006-03-16 | 3M Innovative Properties Company | 2-amino 1h imidazo ring systems and methods |
| JP5209312B2 (ja) * | 2004-09-02 | 2013-06-12 | スリーエム イノベイティブ プロパティズ カンパニー | １−アルコキシ１ｈ−イミダゾ環系および方法 |
| US20080193468A1 (en) * | 2004-09-08 | 2008-08-14 | Children's Medical Center Corporation | Method for Stimulating the Immune Response of Newborns |
| US20070243215A1 (en) * | 2004-10-08 | 2007-10-18 | Miller Richard L | Adjuvant for Dna Vaccines |
| WO2006053166A1 (en) * | 2004-11-12 | 2006-05-18 | Bristol-Myers Squibb Company | 8h-imidazo[4,5-d]thiazolo[4,5-b]pyridine based tricyclic compounds and pharmaceutical compositions comprising same |
| ATE538124T1 (de) | 2004-11-12 | 2012-01-15 | Bristol Myers Squibb Co | Imidazokondensierte tricyclische verbindungen auf thiazoloä4,5-büpyridin-basis und pharmazeutische zusammensetzungen damit |
| WO2006063072A2 (en) * | 2004-12-08 | 2006-06-15 | 3M Innovative Properties Company | Immunomodulatory compositions, combinations and methods |
| US8080560B2 (en) * | 2004-12-17 | 2011-12-20 | 3M Innovative Properties Company | Immune response modifier formulations containing oleic acid and methods |
| AU2005321912B2 (en) | 2004-12-30 | 2012-04-05 | 3M Innovative Properties Company | Treatment for cutaneous metastases |
| AU2005326708C1 (en) | 2004-12-30 | 2012-08-30 | 3M Innovative Properties Company | Substituted 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 |
| AU2005322898B2 (en) * | 2004-12-30 | 2011-11-24 | 3M Innovative Properties Company | Chiral fused (1,2)imidazo(4,5-c) ring compounds |
| AR052447A1 (es) * | 2004-12-30 | 2007-03-21 | 3M Innovative Properties Co | Etansulfonato de 1-(2-metipropil)-1h-imidazo[4,5-c] [1,5] naftiridin-4- amina y metansulfonato de 1-(2- metipropil)-1h-imidazo[4,5 -c] [1,5] naftiridin-4-amina |
| EA200701584A1 (ru) | 2005-01-27 | 2008-02-28 | Альма Матер Студиорум - Университа' Ди Болонья | Органические соединения, применяемые для лечения болезни альцгеймера, их применение и способ получения |
| CA2597092A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| US20080318998A1 (en) * | 2005-02-09 | 2008-12-25 | Coley Pharmaceutical Group, Inc. | Alkyloxy Substituted Thiazoloquinolines and Thiazolonaphthyridines |
| AU2006338521A1 (en) | 2005-02-09 | 2007-10-11 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazolo(4,5-c) ring compounds and methods |
| US8658666B2 (en) * | 2005-02-11 | 2014-02-25 | 3M Innovative Properties Company | Substituted imidazoquinolines and imidazonaphthyridines |
| WO2006086634A2 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| CA2598639A1 (en) * | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazonaphthyridines |
| JP2008538203A (ja) * | 2005-02-23 | 2008-10-16 | 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 | インターフェロンの生合成を優先的に誘導する方法 |
| AU2006216798A1 (en) * | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
| EP1851224A2 (en) * | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
| CA2602098A1 (en) * | 2005-03-14 | 2006-09-21 | Graceway Pharmaceuticals, Llc | Method of treating actinic keratosis |
| AU2006244635A1 (en) * | 2005-04-01 | 2006-11-16 | Coley Pharmaceutical Group, Inc. | Ring closing and related methods and intermediates |
| EP1869043A2 (en) | 2005-04-01 | 2007-12-26 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| CA2602590A1 (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 |
| US20080193474A1 (en) * | 2005-04-25 | 2008-08-14 | Griesgraber George W | Immunostimulatory Compositions |
| US20080234318A1 (en) * | 2005-08-31 | 2008-09-25 | Kristjan Gudmundsson | Chemical Compounds |
| JP2009507856A (ja) * | 2005-09-09 | 2009-02-26 | 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 | Ｎ−｛２−［４−アミノ−２−（エトキシメチル）−１Ｈ−イミダゾ［４，５−ｃ］キノリン−１−イル］−１，１−ジメチルエチル｝メタンスルホンアミドのアミドおよびカルバマート誘導体ならびに方法 |
| 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 |
| 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 |
| JP5247458B2 (ja) * | 2005-11-04 | 2013-07-24 | スリーエム・イノベイティブ・プロパティーズ・カンパニー | ヒドロキシ及びアルコキシ置換１ｈ−イミダゾキノリン及び方法 |
| WO2007079086A1 (en) * | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Pyrazoloalkyl substituted imidazo ring compounds and methods |
| 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 |
| US8088788B2 (en) | 2006-03-15 | 2012-01-03 | 3M Innovative Properties Company | Substituted fused[1,2] imidazo[4,5-c] ring compounds and methods |
| EP2357184B1 (en) | 2006-03-23 | 2015-02-25 | Novartis AG | Imidazoquinoxaline compounds as immunomodulators |
| WO2007143526A2 (en) * | 2006-06-05 | 2007-12-13 | Coley Pharmaceutical Group, Inc. | Substituted tetrahydroimidazonaphthyridines and methods |
| 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 |
| WO2008010963A2 (en) * | 2006-07-18 | 2008-01-24 | 3M Innovative Properties Company | Immune response modifier formulations |
| WO2008016475A2 (en) * | 2006-07-31 | 2008-02-07 | 3M Innovative Properties Company | Immune response modifier compositions and methods |
| WO2008030511A2 (en) * | 2006-09-06 | 2008-03-13 | Coley Pharmaceuticial Group, Inc. | Substituted 3,4,6,7-tetrahydro-5h, 1,2a,4a,8-tetraazacyclopenta[cd]phenalenes |
| US20080149123A1 (en) * | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
| JP2010514679A (ja) * | 2006-12-22 | 2010-05-06 | スリーエム イノベイティブ プロパティズ カンパニー | 制御放出組成物及び方法 |
| WO2008098232A1 (en) * | 2007-02-08 | 2008-08-14 | Graceway Pharmaceuticals, Llc | Methods of treating dermatological disorders and inducing interferon biosynthesis with shorter durations of imiquimod therapy |
| US20100160368A1 (en) * | 2008-08-18 | 2010-06-24 | Gregory Jefferson J | Methods of Treating Dermatological Disorders and Inducing Interferon Biosynthesis With Shorter Durations of Imiquimod Therapy |
| EP2378876B1 (en) | 2008-12-19 | 2018-11-14 | Medicis Pharmaceutical Corporation | Lower dosage strength imiquimod formulations and short dosing regimens for treating actinic keratosis |
| EP2411521B1 (en) | 2009-03-25 | 2015-01-14 | The Board of Regents of The University of Texas System | Compositions for stimulation of mammalian innate immune resistance to pathogens |
| US8349827B2 (en) * | 2009-03-31 | 2013-01-08 | Arqule, Inc. | Substituted dipyrido-pyrimido-diazepine and benzo-pyrido-pyrimido compounds |
| US8511006B2 (en) * | 2009-07-02 | 2013-08-20 | Owens Corning Intellectual Capital, Llc | Building-integrated solar-panel roof element systems |
| AU2010274097B2 (en) | 2009-07-13 | 2016-06-16 | Medicis Pharmaceutical Corporation | Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts |
| US20110033515A1 (en) * | 2009-08-04 | 2011-02-10 | Rst Implanted Cell Technology | Tissue contacting material |
| TW201129565A (en) * | 2010-01-12 | 2011-09-01 | Hoffmann La Roche | Tricyclic heterocyclic compounds, compositions and methods of use thereof |
| WO2011163617A1 (en) | 2010-06-25 | 2011-12-29 | Graceway Pharmaceuticals, Llc | Combination therapy with cryosurgery and low dosage strength imiquimod to treat actinic keratosis |
| HUE033901T2 (en) | 2010-08-17 | 2018-01-29 | 3M Innovative Properties Co | Formulations and formulations for lipidized immune response modifying compounds and related processes |
| JP6415979B2 (ja) | 2011-06-03 | 2018-10-31 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドラジノ１ｈ−イミダゾキノリン−４−アミン及びこれから調製された複合体 |
| CA2838158C (en) | 2011-06-03 | 2019-07-16 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| US20130023736A1 (en) | 2011-07-21 | 2013-01-24 | Stanley Dale Harpstead | Systems for drug delivery and monitoring |
| WO2013040447A2 (en) | 2011-09-14 | 2013-03-21 | Medicis Pharmaceutical Corporation | Combination therapy with low dosage strength imiquimod and photodynamic therapy to treat actinic keratosis |
| ES2727481T3 (es) | 2011-11-30 | 2019-10-16 | Sarepta Therapeutics Inc | Inclusión inducida de exón en atrofia muscular espinal |
| US10076535B2 (en) | 2012-04-27 | 2018-09-18 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Use of CPG oligonucleotides co-formulated with an antibiotic to accelerate wound healing |
| MX359257B (es) | 2012-05-04 | 2018-09-19 | Pfizer | Antígenos asociados a próstata y regímenes de inmunoterapia basados en vacuna. |
| CN112587658A (zh) | 2012-07-18 | 2021-04-02 | 博笛生物科技有限公司 | 癌症的靶向免疫治疗 |
| HUE051988T2 (hu) | 2013-01-07 | 2021-04-28 | Univ Pennsylvania | Készítmények és eljárások bõr T-sejt lymphoma kezelésére |
| EP3632458A1 (en) | 2013-07-26 | 2020-04-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of bacterial infections |
| EP3065741B1 (en) | 2013-11-05 | 2021-09-22 | 3M Innovative Properties Company | Sesame oil based injection formulations |
| CA2933767C (en) | 2013-12-17 | 2018-11-06 | Pfizer Inc. | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| CN105899539B (zh) | 2014-01-10 | 2021-11-09 | 博笛生物科技有限公司 | 用于免疫疗法的化合物和组合物 |
| EP4001311A1 (en) | 2014-07-09 | 2022-05-25 | Birdie Biopharmaceuticals Inc. | Anti-pd-l1 combinations for treating tumors |
| CN112546230A (zh) | 2014-07-09 | 2021-03-26 | 博笛生物科技有限公司 | 用于治疗癌症的联合治疗组合物和联合治疗方法 |
| CN105440135A (zh) | 2014-09-01 | 2016-03-30 | 博笛生物科技有限公司 | 用于治疗肿瘤的抗-pd-l1结合物 |
| WO2016180852A1 (en) | 2015-05-12 | 2016-11-17 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for preparing antigen-specific t cells from an umbilical cord blood sample |
| US11680244B2 (en) | 2015-05-20 | 2023-06-20 | The Regents Of The University Of California | Method for generating human dendritic cells for immunotherapy |
| US10118925B2 (en) | 2015-08-31 | 2018-11-06 | 3M Innovative Properties Company | Imidazo[4,5-c] ring compounds containing substituted guanidine groups |
| AU2016317637B2 (en) | 2015-08-31 | 2019-01-31 | Solventum Intellectual Properties Company | Guanidine substituted imidazo[4,5-c] ring compounds |
| CN108137586B (zh) | 2015-09-14 | 2021-04-13 | 辉瑞大药厂 | 作为LRRK2抑制剂的新颖咪唑并[4,5-c]喹啉和咪唑并[4,5-c][1,5]萘啶衍生物 |
| WO2017059280A1 (en) | 2015-10-02 | 2017-04-06 | The University Of North Carolina At Chapel Hill | Novel pan-tam inhibitors and mer/axl dual inhibitors |
| CN115350279A (zh) | 2016-01-07 | 2022-11-18 | 博笛生物科技有限公司 | 用于治疗肿瘤的抗-her2组合 |
| CN106943596A (zh) | 2016-01-07 | 2017-07-14 | 博笛生物科技（北京）有限公司 | 用于治疗肿瘤的抗-cd20组合 |
| CN106943597A (zh) | 2016-01-07 | 2017-07-14 | 博笛生物科技（北京）有限公司 | 用于治疗肿瘤的抗-egfr组合 |
| JP6883806B2 (ja) * | 2016-03-09 | 2021-06-09 | 国立大学法人大阪大学 | 化合物、及びこれを含む有機半導体材料 |
| CN109562057A (zh) | 2016-05-16 | 2019-04-02 | 传染病研究所 | 聚乙二醇化脂质体和使用方法 |
| IL314130A (en) | 2016-05-16 | 2024-09-01 | Access To Advanced Health Inst | Formulation containing a TLR agonist and methods of use |
| 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 |
| CA3033542A1 (en) | 2016-08-30 | 2018-03-08 | Dana-Farber Cancer Institute, Inc. | Compositions and uses of biomaterials and activators of innate immunity |
| IL266562B1 (en) | 2016-11-09 | 2024-07-01 | Univ Texas | Pharmaceutical compositions for immune regulation adapted for use in the patient sensitive to allergen-induced asthma |
| US11426566B2 (en) | 2016-12-14 | 2022-08-30 | Biora Therapeutics, Inc. | Treatment of a disease of the gastrointestinal tract with a TLR modulator |
| AU2017378398B2 (en) | 2016-12-14 | 2023-02-02 | Biora Therapeutics, Inc. | Treatment of a disease of the gastrointestinal tract with a JAK inhibitor and devices |
| CA3045475A1 (en) | 2016-12-14 | 2018-06-21 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with an il-12/il-23 inhibitor released using an ingestible device |
| CA3045472A1 (en) | 2016-12-14 | 2018-06-21 | Progenity Inc. | Treatment of a disease of the gastrointestinal tract with a smad7 inhibitor |
| EP3554346B1 (en) | 2016-12-14 | 2024-01-31 | Biora Therapeutics, Inc. | Treatment of a disease of the gastrointestinal tract with an immunosuppressant |
| CA3045310A1 (en) | 2016-12-14 | 2018-06-21 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with a chemokine/chemokine receptor inhibitor |
| WO2018160552A1 (en) | 2017-03-01 | 2018-09-07 | 3M Innovative Properties Company | IMIDAZO[4,5-c] RING COMPOUNDS CONTAINING GUANIDINE SUBSTITUTED BENZAMIDE GROUPS |
| US11596670B2 (en) | 2017-03-30 | 2023-03-07 | Biora Therapeutics, Inc. | Treatment of a disease of the gastrointestinal tract with IL-10 or an IL-10 agonist |
| CN118515666A (zh) | 2017-04-27 | 2024-08-20 | 博笛生物科技有限公司 | 2-氨基-喹啉衍生物 |
| AR111760A1 (es) | 2017-05-19 | 2019-08-14 | Novartis Ag | Compuestos y composiciones para el tratamiento de tumores sólidos mediante administración intratumoral |
| JP7080501B2 (ja) | 2017-06-23 | 2022-06-06 | バーディー バイオファーマシューティカルズ インコーポレイテッド | 医薬品組成物 |
| EP4257198A3 (en) | 2017-08-22 | 2023-10-18 | Dynavax Technologies Corporation | Alkyl chain modified imidazoquinoline derivatives as tlr7/8 agonists and uses thereof |
| JP2021503005A (ja) | 2017-11-14 | 2021-02-04 | ダイナバックス テクノロジーズ コーポレイション | Ｔｌｒ７／８アゴニスト化合物の切断可能なコンジュゲート、その調製方法および使用 |
| 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 |
| JP7251893B2 (ja) | 2018-02-28 | 2023-04-04 | スリーエム イノベイティブ プロパティズ カンパニー | Ｎ－１分枝基を有する置換イミダゾ［４，５－ｃ］キノリン化合物 |
| SG11202007518RA (en) | 2018-02-28 | 2020-09-29 | Pfizer | Il-15 variants and uses thereof |
| SG11202010580TA (en) | 2018-05-23 | 2020-12-30 | Pfizer | Antibodies specific for cd3 and uses thereof |
| KR102584675B1 (ko) | 2018-05-23 | 2023-10-05 | 화이자 인코포레이티드 | GUCY2c에 특이적인 항체 및 이의 용도 |
| CA3101277A1 (en) | 2018-05-24 | 2019-11-28 | 3M Innovative Properties Company | N-1 branched cycloalkyl substituted imidazo[4,5-c]quinoline compounds, compositions, and methods |
| CN113166143B (zh) | 2018-11-26 | 2024-06-04 | 舒万诺知识产权公司 | N-1支链烷基醚取代的咪唑并[4,5-c]喹啉化合物、组合物和方法 |
| US20220370606A1 (en) | 2018-12-21 | 2022-11-24 | Pfizer Inc. | Combination Treatments Of Cancer Comprising A TLR Agonist |
| US20220177471A1 (en) | 2019-06-06 | 2022-06-09 | 3M Innovative Properties Company | N-1 branched alkyl substituted imidazo[4,5-c]quinoline compounds, compositions, and methods |
| EP3983408A1 (en) | 2019-06-12 | 2022-04-20 | 3M Innovative Properties Company | Phenethyl substituted imidazo[4,5-c]quinoline compounds with an n-1 branched group |
| WO2021116420A1 (en) | 2019-12-13 | 2021-06-17 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of tlr7 and/or tlr8 agonists for the treatment of leptospirosis |
| WO2021124073A1 (en) | 2019-12-17 | 2021-06-24 | Pfizer Inc. | Antibodies specific for cd47, pd-l1, and uses thereof |
| WO2022009157A1 (en) | 2020-07-10 | 2022-01-13 | Novartis Ag | Lhc165 and spartalizumab combinations for treating solid tumors |
| KR20230022246A (ko) | 2020-07-17 | 2023-02-14 | 화이자 인코포레이티드 | 치료 항체 및 그의 용도 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993009119A1 (en) * | 1991-11-06 | 1993-05-13 | Minnesota Mining And Manufacturing Company | Antiviral 2-ethyl-1h-imidazo(4,5-c)quinolin-4-amines |
| US5627281A (en) * | 1993-07-15 | 1997-05-06 | Minnesota Mining And Manufacturing Company | Intermediate compounds of fused cycloalkylimidazopyridines |
Family Cites Families (97)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3314941A (en) | 1964-06-23 | 1967-04-18 | American Cyanamid Co | Novel substituted pyridodiazepins |
| US3764681A (en) * | 1970-07-08 | 1973-10-09 | Lilly Co Eli | Certain tetrazolo-(1,5-a) quinoline compounds as fungus control agents |
| US3917624A (en) | 1972-09-27 | 1975-11-04 | Pfizer | Process for producing 2-amino-nicotinonitrile intermediates |
| IL73534A (en) * | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| ZA848968B (en) | 1983-11-18 | 1986-06-25 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines |
| 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 |
| US5756747A (en) | 1989-02-27 | 1998-05-26 | Riker Laboratories, Inc. | 1H-imidazo 4,5-c!quinolin-4-amines |
| US5037986A (en) | 1989-03-23 | 1991-08-06 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo[4,5-c]quinolin-4-amines |
| 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 |
| ES2071340T3 (es) | 1990-10-05 | 1995-06-16 | Minnesota Mining & Mfg | Procedimiento para la preparacion de imidazo(4,5-c)quinolin-4-aminas. |
| 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 |
| US5268376A (en) * | 1991-09-04 | 1993-12-07 | Minnesota Mining And Manufacturing Company | 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US5378698A (en) * | 1991-10-21 | 1995-01-03 | Shionogi & Co., Ltd. | Benzothiazepine derivatives |
| IL105325A (en) | 1992-04-16 | 1996-11-14 | Minnesota Mining & Mfg | Immunogen/vaccine adjuvant composition |
| US5395937A (en) | 1993-01-29 | 1995-03-07 | Minnesota Mining And Manufacturing Company | Process for preparing quinoline amines |
| JPH09500128A (ja) | 1993-07-15 | 1997-01-07 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | イミダゾ〔４，５−ｃ〕ピリジン−４−アミン |
| US5352784A (en) | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| US5644063A (en) | 1994-09-08 | 1997-07-01 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]pyridin-4-amine intermediates |
| US5482936A (en) * | 1995-01-12 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-C]quinoline amines |
| US5585612A (en) | 1995-03-20 | 1996-12-17 | Harp Enterprises, Inc. | Method and apparatus for voting |
| JPH09208584A (ja) | 1996-01-29 | 1997-08-12 | Terumo Corp | アミド誘導体、およびそれを含有する医薬製剤、および合成中間体 |
| JPH09255926A (ja) | 1996-03-26 | 1997-09-30 | Diatex Co Ltd | 粘着テープ |
| US5693811A (en) | 1996-06-21 | 1997-12-02 | Minnesota Mining And Manufacturing Company | Process for preparing tetrahdroimidazoquinolinamines |
| US5741908A (en) * | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| DE69737935T2 (de) | 1996-10-25 | 2008-04-03 | Minnesota Mining And Manufacturing Co., St. Paul | Die Immunantwort modifizierende Verbindung zur Behandlung von durch TH2 vermittelten und verwandten Krankheiten |
| PT839810E (pt) * | 1996-11-04 | 2003-01-31 | Bayer Cropscience Sa | 1-poliarilpirazois como pesticidas |
| US5939090A (en) | 1996-12-03 | 1999-08-17 | 3M Innovative Properties Company | Gel formulations for topical drug delivery |
| US6069149A (en) | 1997-01-09 | 2000-05-30 | Terumo Kabushiki Kaisha | Amide derivatives and intermediates for the synthesis thereof |
| UA67760C2 (uk) * | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
| JPH11222432A (ja) | 1998-02-03 | 1999-08-17 | Terumo Corp | インターフェロンを誘起するアミド誘導体を含有する外用剤 |
| JPH11255926A (ja) | 1998-03-13 | 1999-09-21 | Toray Ind Inc | シリコーン成型品およびその製造方法 |
| US6110929A (en) | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| JP2000119271A (ja) | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | １ｈ―イミダゾピリジン誘導体 |
| US6518280B2 (en) * | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
| US20020058674A1 (en) * | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| EP1140091B1 (en) | 1999-01-08 | 2005-09-21 | 3M Innovative Properties Company | Formulations comprising imiquimod or other immune response modifiers for treating cervical dysplasia |
| US6545485B1 (en) * | 1999-01-21 | 2003-04-08 | Radar Engineers | Ultrasonic pinpointer for power system sources of interference |
| US6558951B1 (en) * | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| JP2000247884A (ja) | 1999-03-01 | 2000-09-12 | Sumitomo Pharmaceut Co Ltd | アラキドン酸誘発皮膚疾患治療剤 |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6573273B1 (en) * | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6451810B1 (en) | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6660260B1 (en) * | 1999-09-21 | 2003-12-09 | Mayo Foundation For Medical Education And Research | Bioprosthetic heart valves |
| US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| US20020055517A1 (en) | 2000-09-15 | 2002-05-09 | 3M Innovative Properties Company | Methods for delaying recurrence of herpes virus symptoms |
| JP2002145777A (ja) | 2000-11-06 | 2002-05-22 | Sumitomo Pharmaceut Co Ltd | アラキドン酸誘発皮膚疾患治療剤 |
| US6664260B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Heterocyclic ether substituted imidazoquinolines |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6677347B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US6660735B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| US6664265B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| UA74593C2 (en) | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| US6660747B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| AU3249802A (en) * | 2000-12-08 | 2002-06-18 | 3M Innovative Properties Co | Screening method for identifying compounds that selectively induce interferon alpha |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| UA74852C2 (en) * | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6677348B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| CA2449754A1 (en) | 2001-06-15 | 2002-12-27 | 3M Innovative Properties Company | Immune response modifiers for the treatment of periodontal disease |
| WO2003020889A2 (en) | 2001-08-30 | 2003-03-13 | 3M Innovative Properties Company | Methods of maturing plasmacytoid dendritic cells using immune response modifier molecules |
| US6667347B2 (en) * | 2001-09-14 | 2003-12-23 | Chevron U.S.A. Inc. | Scrubbing CO2 from methane-containing gases using an aqueous stream |
| WO2003094836A2 (en) * | 2001-10-12 | 2003-11-20 | University Of Iowa Research Foundation | Methods and products for enhancing immune responses using imidazoquinoline compounds |
| US20040014779A1 (en) * | 2001-11-16 | 2004-01-22 | 3M Innovative Properties Company | Methods and compositions related to IRM compounds and toll-like recptor pathways |
| CA2467828C (en) * | 2001-11-29 | 2011-10-04 | 3M Innovative Properties Company | Pharmaceutical formulations comprising an immune response modifier |
| US6677349B1 (en) * | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| SI1478327T1 (sl) * | 2002-02-22 | 2015-08-31 | Meda Ab | Metoda za zmanjšanje in zdravljenje imunosupresije, inducirane z UV-B |
| 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 |
| AU2003237386A1 (en) * | 2002-06-07 | 2003-12-22 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| WO2004032829A2 (en) * | 2002-08-15 | 2004-04-22 | 3M Innovative Properties Company | Immunostimulatory compositions and methods of stimulating an immune response |
| US6818650B2 (en) * | 2002-09-26 | 2004-11-16 | 3M Innovative Properties Company | 1H-imidazo dimers |
| EP1572236A4 (en) * | 2002-11-14 | 2007-01-03 | Pintex Pharmaceuticals Inc | PINE RATE1 IN HEALTHY FABRIC AND IN CANCER FABRIC |
| AU2003287316A1 (en) * | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Assays relating to toll-like receptor activity |
| AU2003287324A1 (en) * | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Gene expression systems and recombinant cell lines |
| EP1590348A1 (en) * | 2002-12-20 | 2005-11-02 | 3M Innovative Properties Company | Aryl / hetaryl substituted imidazoquinolines |
| JP2006512391A (ja) * | 2002-12-30 | 2006-04-13 | スリーエム イノベイティブ プロパティズ カンパニー | 組み合わせ免疫賦活薬 |
| WO2004071459A2 (en) * | 2003-02-13 | 2004-08-26 | 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 |
| AU2004218349A1 (en) * | 2003-03-04 | 2004-09-16 | 3M Innovative Properties Company | Prophylactic treatment of UV-induced epidermal neoplasia |
| CA2517655A1 (en) * | 2003-03-07 | 2004-09-23 | 3M Innovative Properties Company | 1-amino 1h-imidazoquinolines |
| US8426457B2 (en) * | 2003-03-13 | 2013-04-23 | Medicis Pharmaceutical Corporation | Methods of improving skin quality |
| AU2004220465A1 (en) * | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Method of tattoo removal |
| US7699057B2 (en) * | 2003-03-13 | 2010-04-20 | 3M Innovative Properties Company | Methods for treating skin lesions |
| US20040192585A1 (en) * | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
| US20040191833A1 (en) * | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Selective activation of cellular activities mediated through a common toll-like receptor |
| AU2004244962A1 (en) * | 2003-04-10 | 2004-12-16 | 3M Innovative Properties Company | Delivery of immune response modifier compounds using metal-containing particulate support materials |
| EP1617845A4 (en) * | 2003-04-28 | 2006-09-20 | 3M Innovative Properties Co | COMPOSITIONS AND METHODS FOR INDUCING OPOID RECEPTORS |
| OA13310A (en) * | 2003-09-05 | 2007-04-13 | Anadys Pharmaceuticals Inc | TLR7 ligands for the treatment of hepatitis C. |
| AR052447A1 (es) * | 2004-12-30 | 2007-03-21 | 3M Innovative Properties Co | Etansulfonato de 1-(2-metipropil)-1h-imidazo[4,5-c] [1,5] naftiridin-4- amina y metansulfonato de 1-(2- metipropil)-1h-imidazo[4,5 -c] [1,5] naftiridin-4-amina |
-
1998
- 1998-11-12 UA UA2000074070A patent/UA67760C2/uk unknown
- 1998-12-11 DE DE69835844T patent/DE69835844T2/de not_active Expired - Fee Related
- 1998-12-11 AT AT04022440T patent/ATE333456T1/de active
- 1998-12-11 DE DE69826518T patent/DE69826518T2/de not_active Expired - Fee Related
- 1998-12-11 KR KR1020037016103A patent/KR100563175B1/ko not_active IP Right Cessation
- 1998-12-11 ES ES04022440T patent/ES2270249T3/es not_active Expired - Lifetime
- 1998-12-11 RU RU2003126258/04A patent/RU2314307C2/ru active
- 1998-12-11 DK DK04022441T patent/DK1512686T3/da active
- 1998-12-11 SI SI9830868T patent/SI1512686T1/sl unknown
- 1998-12-11 AU AU19123/99A patent/AU753864B2/en not_active Ceased
- 1998-12-11 HU HU0101155A patent/HUP0101155A3/hu unknown
- 1998-12-11 SK SK835-2000A patent/SK285872B6/sk not_active IP Right Cessation
- 1998-12-11 RU RU2000114496/04A patent/RU2221798C2/ru active
- 1998-12-11 SK SK5035-2007A patent/SK286304B6/sk not_active IP Right Cessation
- 1998-12-11 KR KR1020037016102A patent/KR100642702B1/ko not_active IP Right Cessation
- 1998-12-11 CA CA2311456A patent/CA2311456C/en not_active Expired - Lifetime
- 1998-12-11 NZ NZ504776A patent/NZ504776A/en unknown
- 1998-12-11 DE DE69835309T patent/DE69835309T2/de not_active Expired - Lifetime
- 1998-12-11 KR KR1020007006369A patent/KR100642703B1/ko not_active IP Right Cessation
- 1998-12-11 WO PCT/US1998/026473 patent/WO1999029693A1/en active Application Filing
- 1998-12-11 PT PT04022440T patent/PT1512685E/pt unknown
- 1998-12-11 EE EEP200000349A patent/EE04314B1/xx not_active IP Right Cessation
- 1998-12-11 US US09/210,114 patent/US6194425B1/en not_active Expired - Fee Related
- 1998-12-11 PL PL98341159A patent/PL193915B1/pl not_active IP Right Cessation
- 1998-12-11 ES ES04022441T patent/ES2273138T3/es not_active Expired - Lifetime
- 1998-12-11 AT AT04022441T patent/ATE338757T1/de not_active IP Right Cessation
- 1998-12-11 PT PT04022441T patent/PT1512686E/pt unknown
- 1998-12-11 BR BR9814275-5A patent/BR9814275A/pt not_active IP Right Cessation
- 1998-12-11 CN CNB988135639A patent/CN1154647C/zh not_active Expired - Fee Related
- 1998-12-11 EP EP98963888A patent/EP1040112B1/en not_active Expired - Lifetime
- 1998-12-11 JP JP2000524286A patent/JP4283438B2/ja not_active Expired - Fee Related
- 1998-12-11 CZ CZ2007-268A patent/CZ307184B6/cs not_active IP Right Cessation
- 1998-12-11 ES ES98963888T patent/ES2227902T3/es not_active Expired - Lifetime
- 1998-12-11 IL IL13655698A patent/IL136556A0/xx active IP Right Grant
- 1998-12-11 AT AT98963888T patent/ATE277046T1/de not_active IP Right Cessation
- 1998-12-11 RU RU2003126259/04A patent/RU2312867C2/ru not_active IP Right Cessation
- 1998-12-11 PT PT98963888T patent/PT1040112E/pt unknown
- 1998-12-11 TR TR2000/01705T patent/TR200001705T2/xx unknown
-
2000
- 2000-05-24 NO NO20002663A patent/NO316687B1/no not_active IP Right Cessation
- 2000-06-02 HR HR20000363A patent/HRP20000363B1/xx not_active IP Right Cessation
- 2000-06-05 IL IL136556A patent/IL136556A/en not_active IP Right Cessation
- 2000-11-06 US US09/706,990 patent/US6514985B1/en not_active Expired - Fee Related
-
2001
- 2001-08-31 US US09/945,197 patent/US6624172B2/en not_active Expired - Lifetime
-
2002
- 2002-06-27 US US10/185,387 patent/US6693113B2/en not_active Expired - Lifetime
- 2002-06-27 US US10/184,304 patent/US6638944B2/en not_active Expired - Fee Related
- 2002-10-07 US US10/265,956 patent/US6699878B2/en not_active Expired - Fee Related
-
2003
- 2003-04-02 US US10/405,321 patent/US6747040B2/en not_active Expired - Fee Related
- 2003-04-03 US US10/406,181 patent/US6797716B2/en not_active Expired - Lifetime
- 2003-12-19 NO NO20035718A patent/NO328045B1/no not_active IP Right Cessation
- 2003-12-19 NO NO20035719A patent/NO20035719D0/no unknown
-
2004
- 2004-04-14 US US10/824,232 patent/US6894165B2/en not_active Expired - Fee Related
- 2004-12-03 US US11/004,674 patent/US6949646B2/en not_active Expired - Lifetime
-
2005
- 2005-04-21 HK HK05103436A patent/HK1070655A1/xx not_active IP Right Cessation
- 2005-07-25 US US11/188,418 patent/US7038051B2/en not_active Expired - Lifetime
- 2005-12-12 JP JP2005358302A patent/JP4203067B2/ja not_active Expired - Fee Related
-
2006
- 2006-02-13 US US11/276,074 patent/US7335773B2/en not_active Expired - Fee Related
- 2006-09-14 IL IL178092A patent/IL178092A/en not_active IP Right Cessation
- 2006-09-14 IL IL178091A patent/IL178091A/en not_active IP Right Cessation
-
2007
- 2007-03-28 US US11/692,701 patent/US20070167481A1/en not_active Abandoned
- 2007-07-11 JP JP2007181872A patent/JP2007262093A/ja not_active Withdrawn
- 2007-12-06 US US11/999,602 patent/US7678918B2/en not_active Expired - Fee Related
- 2007-12-26 JP JP2007335120A patent/JP2008115190A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993009119A1 (en) * | 1991-11-06 | 1993-05-13 | Minnesota Mining And Manufacturing Company | Antiviral 2-ethyl-1h-imidazo(4,5-c)quinolin-4-amines |
| US5627281A (en) * | 1993-07-15 | 1997-05-06 | Minnesota Mining And Manufacturing Company | Intermediate compounds of fused cycloalkylimidazopyridines |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CZ307184B6 (cs) | 2-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naftyridin-4-amin a farmaceutická kompozice s jeho obsahem | |
| EP1343784B1 (en) | UREA SUBSTITUTED IMIDAZOQUINOLINE ETHERS and pharmaceutical compositions comprising the same. | |
| US6660747B2 (en) | Amido ether substituted imidazoquinolines | |
| US7214675B2 (en) | Urea substituted imidazoquinoline ethers | |
| US20020107262A1 (en) | Substituted imidazopyridines | |
| AU2002232497A1 (en) | Urea substituted imidazoquinoline ethers | |
| PT1198233E (pt) | Imidazoquinilinas substituídas com sulfonamida e sulfamida | |
| AU2002232482A1 (en) | Amido ether substituted imidazoquinolines | |
| CZ20031593A3 (cs) | Substituované imidazopyridiny | |
| AU2002239517A1 (en) | Sulfonamido ether substituted imidazoquinolines | |
| EP1512686B1 (en) | Imidazonaphthyridines and their use in inducing cytokine biosynthesis | |
| CZ20002158A3 (cs) | Imidazonaftyridiny a jejich použití při indukci biosyntézy cytokinu | |
| IL170791A (en) | Method of electromagnetically shielding buildings and bitumen panels useful therein |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 19981211 |