AU2003299863B2 - Immunostimulatory compositions and methods of stimulating an immune response - Google Patents
Immunostimulatory compositions and methods of stimulating an immune response Download PDFInfo
- Publication number
- AU2003299863B2 AU2003299863B2 AU2003299863A AU2003299863A AU2003299863B2 AU 2003299863 B2 AU2003299863 B2 AU 2003299863B2 AU 2003299863 A AU2003299863 A AU 2003299863A AU 2003299863 A AU2003299863 A AU 2003299863A AU 2003299863 B2 AU2003299863 B2 AU 2003299863B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- substituted
- aryl
- amine
- alkenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 230000003308 immunostimulating effect Effects 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 230000028993 immune response Effects 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims description 22
- 230000004936 stimulating effect Effects 0.000 title claims description 8
- 230000000890 antigenic effect Effects 0.000 claims abstract description 38
- 239000003607 modifier Substances 0.000 claims abstract description 26
- -1 imidazoquinoline amine Chemical class 0.000 claims description 78
- 108091007433 antigens Proteins 0.000 claims description 69
- 102000036639 antigens Human genes 0.000 claims description 69
- 239000000427 antigen Substances 0.000 claims description 68
- 229940124669 imidazoquinoline Drugs 0.000 claims description 16
- 125000005647 linker group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical class 0.000 claims description 13
- 125000000623 heterocyclic group Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000000338 in vitro Methods 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 11
- 238000010168 coupling process Methods 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000000556 agonist Substances 0.000 claims description 5
- 210000000628 antibody-producing cell Anatomy 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 3
- 102000029797 Prion Human genes 0.000 claims description 3
- 108091000054 Prion Proteins 0.000 claims description 3
- 241000700605 Viruses Species 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 108010060804 Toll-Like Receptor 4 Proteins 0.000 claims description 2
- 102000008237 Toll-Like Receptor 6 Human genes 0.000 claims description 2
- 108010060826 Toll-Like Receptor 6 Proteins 0.000 claims description 2
- 108010060825 Toll-Like Receptor 7 Proteins 0.000 claims description 2
- 108010060752 Toll-Like Receptor 8 Proteins 0.000 claims description 2
- 102100024333 Toll-like receptor 2 Human genes 0.000 claims description 2
- 108010060888 Toll-like receptor 2 Proteins 0.000 claims description 2
- 102100039360 Toll-like receptor 4 Human genes 0.000 claims description 2
- 102100039390 Toll-like receptor 7 Human genes 0.000 claims description 2
- 102100033110 Toll-like receptor 8 Human genes 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000002773 nucleotide Substances 0.000 claims description 2
- 125000003729 nucleotide group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 238000009792 diffusion process Methods 0.000 claims 1
- 229940092253 ovalbumin Drugs 0.000 description 69
- 108010058846 Ovalbumin Proteins 0.000 description 60
- 239000000243 solution Substances 0.000 description 51
- 241000699670 Mus sp. Species 0.000 description 43
- 210000001744 T-lymphocyte Anatomy 0.000 description 35
- 230000003053 immunization Effects 0.000 description 34
- 238000002649 immunization Methods 0.000 description 31
- 206010028980 Neoplasm Diseases 0.000 description 26
- 210000004027 cell Anatomy 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 101100167439 Arabidopsis thaliana CLPC1 gene Proteins 0.000 description 13
- 101100509022 Arabidopsis thaliana IRM1 gene Proteins 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- JVJGCCBAOOWGEO-RUTPOYCXSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-4-amino-2-[[(2s,3s)-2-[[(2s,3s)-2-[[(2s)-2-azaniumyl-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxylatobutanoyl]amino]-6-azaniumy Chemical compound OC[C@H](N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(O)=O)CC1=CC=CC=C1 JVJGCCBAOOWGEO-RUTPOYCXSA-N 0.000 description 12
- 210000001266 CD8-positive T-lymphocyte Anatomy 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 108090000765 processed proteins & peptides Proteins 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
- 102000004169 proteins and genes Human genes 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000006260 foam Substances 0.000 description 10
- 230000004044 response Effects 0.000 description 10
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 9
- 239000002953 phosphate buffered saline Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- 239000004971 Cross linker Substances 0.000 description 8
- 210000000612 antigen-presenting cell Anatomy 0.000 description 8
- 230000003993 interaction Effects 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 102000004196 processed proteins & peptides Human genes 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 108090000695 Cytokines Proteins 0.000 description 7
- 102000004127 Cytokines Human genes 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 201000001441 melanoma Diseases 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- 102000002689 Toll-like receptor Human genes 0.000 description 6
- 108020000411 Toll-like receptor Proteins 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 210000001165 lymph node Anatomy 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 210000000952 spleen Anatomy 0.000 description 6
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 108091034117 Oligonucleotide Proteins 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000000684 flow cytometry Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- GSSMIHQEWAQUPM-AOLPDKKJSA-N ovalbumin peptide Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)[C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C1=CN=CN1 GSSMIHQEWAQUPM-AOLPDKKJSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229960005486 vaccine Drugs 0.000 description 4
- 239000012646 vaccine adjuvant Substances 0.000 description 4
- 229940124931 vaccine adjuvant Drugs 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- 102100032912 CD44 antigen Human genes 0.000 description 3
- 108090000288 Glycoproteins Proteins 0.000 description 3
- 102000003886 Glycoproteins Human genes 0.000 description 3
- 101000868273 Homo sapiens CD44 antigen Proteins 0.000 description 3
- 102000043129 MHC class I family Human genes 0.000 description 3
- 108091054437 MHC class I family Proteins 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000003368 amide group Chemical class 0.000 description 3
- 210000003719 b-lymphocyte Anatomy 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 229960002685 biotin Drugs 0.000 description 3
- 239000011616 biotin Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000016396 cytokine production Effects 0.000 description 3
- 210000004443 dendritic cell Anatomy 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 238000003306 harvesting Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 208000002672 hepatitis B Diseases 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 210000002865 immune cell Anatomy 0.000 description 3
- 210000000987 immune system Anatomy 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 230000021633 leukocyte mediated immunity Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 210000004989 spleen cell Anatomy 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- SVBZCXQPNPURIX-UHFFFAOYSA-N 1-(2-amino-2-methylpropyl)-2-(ethoxymethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)N)C3=C(N)N=C21 SVBZCXQPNPURIX-UHFFFAOYSA-N 0.000 description 2
- JEFFGDGZXNZKEB-UHFFFAOYSA-N 1-[2-(2-aminoethoxy)ethyl]-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCOCCN)C3=C(N)N=C21 JEFFGDGZXNZKEB-UHFFFAOYSA-N 0.000 description 2
- GCGNWZMOENODOJ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-h]quinoline Chemical class C1C=C2C=CC=NC2=C2C1NCN2 GCGNWZMOENODOJ-UHFFFAOYSA-N 0.000 description 2
- PMZRURHMILNZMV-UHFFFAOYSA-N 2-[(2-azidooxybenzoyl)amino]hexanoic acid Chemical compound CCCCC(C(O)=O)NC(=O)C1=CC=CC=C1ON=[N+]=[N-] PMZRURHMILNZMV-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- ZRFUZDDJSQVQBY-UHFFFAOYSA-N 4-chloro-3-nitroquinoline Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CN=C21 ZRFUZDDJSQVQBY-UHFFFAOYSA-N 0.000 description 2
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical class NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 2
- 101100152731 Arabidopsis thaliana TH2 gene Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108090001008 Avidin Proteins 0.000 description 2
- 206010004146 Basal cell carcinoma Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010008631 Cholera Diseases 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 208000032027 Essential Thrombocythemia Diseases 0.000 description 2
- 208000005176 Hepatitis C Diseases 0.000 description 2
- 208000009889 Herpes Simplex Diseases 0.000 description 2
- 102000008949 Histocompatibility Antigens Class I Human genes 0.000 description 2
- 108010088652 Histocompatibility Antigens Class I Proteins 0.000 description 2
- 108010002352 Interleukin-1 Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 description 2
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 2
- 102100040247 Tumor necrosis factor Human genes 0.000 description 2
- 208000003152 Yellow Fever Diseases 0.000 description 2
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical group 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- 210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- OFFQPEBWIQOAIP-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O.CCCCCCCCCCCCCCCC(N)=O OFFQPEBWIQOAIP-UHFFFAOYSA-N 0.000 description 2
- 229940081141 hexadecanamide Drugs 0.000 description 2
- 230000028996 humoral immune response Effects 0.000 description 2
- 230000002519 immonomodulatory effect Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 206010022000 influenza Diseases 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 230000001613 neoplastic effect Effects 0.000 description 2
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 2
- CTRLRINCMYICJO-UHFFFAOYSA-N phenyl azide Chemical compound [N-]=[N+]=NC1=CC=CC=C1 CTRLRINCMYICJO-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 2
- 201000010153 skin papilloma Diseases 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- PPHLYKFEQMEWND-UHFFFAOYSA-N tert-butyl n-[1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]carbamate Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)NC(=O)OC(C)(C)C)C3=C(N)N=C21 PPHLYKFEQMEWND-UHFFFAOYSA-N 0.000 description 2
- VULKFBHOEKTQSF-UHFFFAOYSA-N tert-butyl n-[2-(2-aminoethoxy)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCOCCN VULKFBHOEKTQSF-UHFFFAOYSA-N 0.000 description 2
- OIGBULWLGULHNH-UHFFFAOYSA-N tert-butyl n-[2-(2-azidoethoxy)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCOCCN=[N+]=[N-] OIGBULWLGULHNH-UHFFFAOYSA-N 0.000 description 2
- KSFVNEXYCULLEJ-UHFFFAOYSA-N tert-butyl n-[2-(2-hydroxyethoxy)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCOCCO KSFVNEXYCULLEJ-UHFFFAOYSA-N 0.000 description 2
- JAQSDPOQNDCKFI-UHFFFAOYSA-N tert-butyl n-[2-[2-[(3-aminoquinolin-4-yl)amino]ethoxy]ethyl]carbamate Chemical compound C1=CC=C2C(NCCOCCNC(=O)OC(C)(C)C)=C(N)C=NC2=C1 JAQSDPOQNDCKFI-UHFFFAOYSA-N 0.000 description 2
- AYXPXAHRVRCZFV-UHFFFAOYSA-N tert-butyl n-[2-[2-[(3-nitroquinolin-4-yl)amino]ethoxy]ethyl]carbamate Chemical compound C1=CC=C2C(NCCOCCNC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=NC2=C1 AYXPXAHRVRCZFV-UHFFFAOYSA-N 0.000 description 2
- DKXHXQZSFXDJMQ-UHFFFAOYSA-N tert-butyl n-[2-[2-[2-(2-methoxyethyl)-5-oxidoimidazo[4,5-c]quinolin-5-ium-1-yl]ethoxy]ethyl]carbamate Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCOCCNC(=O)OC(C)(C)C)C3=C[N+]([O-])=C21 DKXHXQZSFXDJMQ-UHFFFAOYSA-N 0.000 description 2
- GRBPJBQMZFHFJK-UHFFFAOYSA-N tert-butyl n-[2-methyl-1-[(3-nitroquinolin-4-yl)amino]propan-2-yl]carbamate Chemical compound C1=CC=C2C(NCC(C)(C)NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=NC2=C1 GRBPJBQMZFHFJK-UHFFFAOYSA-N 0.000 description 2
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 201000008827 tuberculosis Diseases 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- 241000701161 unidentified adenovirus Species 0.000 description 2
- 238000003260 vortexing Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OPCJOXGBLDJWRM-UHFFFAOYSA-N 1,2-diamino-2-methylpropane Chemical compound CC(C)(N)CN OPCJOXGBLDJWRM-UHFFFAOYSA-N 0.000 description 1
- QLHVOTQJVQFWHB-UHFFFAOYSA-N 1-[2-[(2-azidooxybenzoyl)amino]hexanoyloxy]-3-hydroxy-2,5-dioxopyrrolidine-3-sulfonic acid Chemical compound N(=[N+]=[N-])OC=1C(C(=O)NC(C(=O)ON2C(C(CC2=O)(S(=O)(=O)O)O)=O)CCCC)=CC=CC1 QLHVOTQJVQFWHB-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 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 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- ZDLSZXWATPDDQS-UHFFFAOYSA-N 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethyl methanesulfonate Chemical compound CC(C)(C)OC(=O)NCCOCCOS(C)(=O)=O ZDLSZXWATPDDQS-UHFFFAOYSA-N 0.000 description 1
- SKIIKRJAQOSWFT-UHFFFAOYSA-N 2-[3-[1-(2,2-difluoroethyl)piperidin-4-yl]oxy-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound FC(CN1CCC(CC1)OC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CC2=C(CC1)NN=N2)F SKIIKRJAQOSWFT-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
- MJWNZUXIXLDUET-UHFFFAOYSA-N 2-methyl-1-n-(3-nitroquinolin-4-yl)propane-1,2-diamine Chemical compound C1=CC=C2C(NCC(C)(N)C)=C([N+]([O-])=O)C=NC2=C1 MJWNZUXIXLDUET-UHFFFAOYSA-N 0.000 description 1
- JSMDUOFOPDSKIQ-UHFFFAOYSA-N 3-methoxypropanoyl chloride Chemical compound COCCC(Cl)=O JSMDUOFOPDSKIQ-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 206010059313 Anogenital warts Diseases 0.000 description 1
- 206010073941 Anorectal human papilloma virus infection Diseases 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 208000012657 Atopic disease Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 102100021943 C-C motif chemokine 2 Human genes 0.000 description 1
- 101710155857 C-C motif chemokine 2 Proteins 0.000 description 1
- 238000011740 C57BL/6 mouse Methods 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 206010008263 Cervical dysplasia Diseases 0.000 description 1
- 201000006082 Chickenpox Diseases 0.000 description 1
- 241000606161 Chlamydia Species 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 208000000907 Condylomata Acuminata Diseases 0.000 description 1
- 241000711573 Coronaviridae Species 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
- 241000701022 Cytomegalovirus Species 0.000 description 1
- 108010041986 DNA Vaccines Proteins 0.000 description 1
- 208000001490 Dengue Diseases 0.000 description 1
- 206010012310 Dengue fever Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010014596 Encephalitis Japanese B Diseases 0.000 description 1
- 241000709661 Enterovirus Species 0.000 description 1
- 206010014950 Eosinophilia Diseases 0.000 description 1
- 208000004729 Feline Leukemia Diseases 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 201000002563 Histoplasmosis Diseases 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
- 241000701806 Human papillomavirus Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 208000002979 Influenza in Birds Diseases 0.000 description 1
- 102000002227 Interferon Type I Human genes 0.000 description 1
- 108010014726 Interferon Type I Proteins 0.000 description 1
- 102000008070 Interferon-gamma Human genes 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 108090000174 Interleukin-10 Proteins 0.000 description 1
- 108010065805 Interleukin-12 Proteins 0.000 description 1
- 108090000978 Interleukin-4 Proteins 0.000 description 1
- 108010002616 Interleukin-5 Proteins 0.000 description 1
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- 108090001007 Interleukin-8 Proteins 0.000 description 1
- 201000005807 Japanese encephalitis Diseases 0.000 description 1
- 241000710842 Japanese encephalitis virus Species 0.000 description 1
- 108090001090 Lectins Proteins 0.000 description 1
- 102000004856 Lectins Human genes 0.000 description 1
- 208000004554 Leishmaniasis Diseases 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 201000005505 Measles Diseases 0.000 description 1
- 206010027209 Meningitis cryptococcal Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 101710151805 Mitochondrial intermediate peptidase 1 Proteins 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 208000005647 Mumps Diseases 0.000 description 1
- 241000186367 Mycobacterium avium Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 108010075205 OVA-8 Proteins 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 241001631646 Papillomaviridae Species 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 241000233870 Pneumocystis Species 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 240000006413 Prunus persica var. persica Species 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 206010037742 Rabies Diseases 0.000 description 1
- 102000007056 Recombinant Fusion Proteins Human genes 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 241000725643 Respiratory syncytial virus Species 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 241000702670 Rotavirus Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 208000001203 Smallpox Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- 201000005485 Toxoplasmosis Diseases 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 208000037386 Typhoid Diseases 0.000 description 1
- 206010046980 Varicella Diseases 0.000 description 1
- 241000870995 Variola Species 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 208000009621 actinic keratosis Diseases 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 1
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 208000004631 alopecia areata Diseases 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 208000025009 anogenital human papillomavirus infection Diseases 0.000 description 1
- 201000004201 anogenital venereal wart Diseases 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000009833 antibody interaction Effects 0.000 description 1
- 230000009831 antigen interaction Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 229940121357 antivirals Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000004305 biphenyl Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 210000002798 bone marrow cell Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 229940030156 cell vaccine Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 229940028617 conventional vaccine Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 201000007241 cutaneous T cell lymphoma Diseases 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000004163 cytometry Methods 0.000 description 1
- 208000025729 dengue disease Diseases 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000012458 free base 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
- 125000002541 furyl group Chemical group 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 201000009277 hairy cell leukemia Diseases 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 208000005252 hepatitis A Diseases 0.000 description 1
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 1
- 125000005367 heteroarylalkylthio group Chemical group 0.000 description 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 1
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- 230000004727 humoral immunity Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000005232 imidazopyridines Chemical class 0.000 description 1
- 229960002751 imiquimod Drugs 0.000 description 1
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000016784 immunoglobulin production Effects 0.000 description 1
- 238000012606 in vitro cell culture Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000037797 influenza A Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229960003130 interferon gamma Drugs 0.000 description 1
- 208000020082 intraepithelial neoplasia Diseases 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 208000011379 keloid formation Diseases 0.000 description 1
- 239000002523 lectin Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000001638 lipofection Methods 0.000 description 1
- 229920006008 lipopolysaccharide Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229960005037 meningococcal vaccines Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 208000008588 molluscum contagiosum Diseases 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 208000010805 mumps infectious disease Diseases 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229960001973 pneumococcal vaccines Drugs 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- 239000002157 polynucleotide Substances 0.000 description 1
- 102000040430 polynucleotide Human genes 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 201000005404 rubella Diseases 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- QJZOFJMBDNNMQK-UHFFFAOYSA-N tert-butyl n-[2-[2-[2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]ethoxy]ethyl]carbamate Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCOCCNC(=O)OC(C)(C)C)C3=CN=C21 QJZOFJMBDNNMQK-UHFFFAOYSA-N 0.000 description 1
- UPYNLGBEILFEFA-UHFFFAOYSA-N tert-butyl n-[2-[2-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]ethoxy]ethyl]carbamate Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCOCCNC(=O)OC(C)(C)C)C3=C(N)N=C21 UPYNLGBEILFEFA-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229960002109 tuberculosis vaccine Drugs 0.000 description 1
- 201000008297 typhoid fever Diseases 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/385—Haptens or antigens, bound to carriers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/60—Medicinal preparations containing antigens or antibodies characteristics by the carrier linked to the antigen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40384602P | 2002-08-15 | 2002-08-15 | |
| US60/403,846 | 2002-08-15 | ||
| PCT/US2003/025523 WO2004032829A2 (en) | 2002-08-15 | 2003-08-14 | Immunostimulatory compositions and methods of stimulating an immune response |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2003299863A2 AU2003299863A2 (en) | 2004-05-04 |
| AU2003299863A1 AU2003299863A1 (en) | 2004-05-04 |
| AU2003299863B2 true AU2003299863B2 (en) | 2009-09-24 |
Family
ID=32093749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003299863A Ceased AU2003299863B2 (en) | 2002-08-15 | 2003-08-14 | Immunostimulatory compositions and methods of stimulating an immune response |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7427629B2 (OSRAM) |
| EP (2) | EP1545597B1 (OSRAM) |
| JP (2) | JP4860923B2 (OSRAM) |
| KR (1) | KR101088615B1 (OSRAM) |
| CN (1) | CN1671412B (OSRAM) |
| AT (1) | ATE488246T1 (OSRAM) |
| AU (1) | AU2003299863B2 (OSRAM) |
| BR (1) | BR0313587A (OSRAM) |
| CA (1) | CA2495570C (OSRAM) |
| DE (1) | DE60335010D1 (OSRAM) |
| DK (1) | DK1545597T3 (OSRAM) |
| ES (1) | ES2355819T3 (OSRAM) |
| MX (1) | MXPA05001647A (OSRAM) |
| NZ (1) | NZ538812A (OSRAM) |
| PT (1) | PT1545597E (OSRAM) |
| WO (1) | WO2004032829A2 (OSRAM) |
Families Citing this family (156)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| 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 |
| CA2598144A1 (en) * | 2000-12-08 | 2006-08-31 | 3M Innovative Properties Company | Compositions and methods for targeted delivery of immune response modifiers |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| UA75622C2 (en) | 2000-12-08 | 2006-05-15 | 3M Innovative Properties Co | Aryl ether substituted imidazoquinolines, pharmaceutical composition based thereon |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| WO2004080430A2 (en) * | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Methods of improving skin quality |
| 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 |
| ES2543710T3 (es) | 2002-04-04 | 2015-08-21 | Zoetis Belgium S.A. | Oligorribonucleótidos inmunoestimulantes que contienen G y U |
| AU2003237386A1 (en) | 2002-06-07 | 2003-12-22 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| EP1590348A1 (en) | 2002-12-20 | 2005-11-02 | 3M Innovative Properties Company | Aryl / hetaryl substituted imidazoquinolines |
| JP2006523452A (ja) * | 2003-03-25 | 2006-10-19 | スリーエム イノベイティブ プロパティズ カンパニー | 共通のＴｏｌｌ様受容体を通じて媒介される細胞活性の選択的活性化 |
| US20040265351A1 (en) * | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| WO2005001022A2 (en) * | 2003-04-10 | 2005-01-06 | 3M Innovative Properties Company | Methods and compositions for enhancing immune response |
| US6943255B2 (en) * | 2003-06-06 | 2005-09-13 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| US20050032829A1 (en) * | 2003-06-06 | 2005-02-10 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| AU2004264336B2 (en) * | 2003-08-05 | 2010-12-23 | 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 |
| WO2005018555A2 (en) * | 2003-08-14 | 2005-03-03 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
| 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 |
| WO2005018574A2 (en) * | 2003-08-25 | 2005-03-03 | 3M Innovative Properties Company | Immunostimulatory combinations and treatments |
| PH12006500401A1 (en) | 2003-08-27 | 2005-03-10 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| EP1660026A4 (en) | 2003-09-05 | 2008-07-16 | 3M Innovative Properties Co | TREATMENT FOR CD5 + B CELL LYMPHOMA |
| WO2005029037A2 (en) * | 2003-09-17 | 2005-03-31 | 3M Innovative Properties Company | Selective modulation of tlr gene expression |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| CA2540598C (en) | 2003-10-03 | 2013-09-24 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| EP1673087B1 (en) | 2003-10-03 | 2015-05-13 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| EP1680080A4 (en) * | 2003-10-31 | 2007-10-31 | 3M Innovative Properties Co | NEUTROPHILIC ACTIVATION THROUGH COMPOUNDS TO MODIFY THE IMMUNE RESPONSE |
| EP1685129A4 (en) * | 2003-11-14 | 2008-10-22 | 3M Innovative Properties Co | OXIMSUBSTITUTED IMIDAZORING CONNECTIONS |
| WO2005048945A2 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| CA2547020C (en) | 2003-11-25 | 2014-03-25 | 3M Innovative Properties Company | 1h-imidazo[4,5-c]pyridine-4-amine derivatives as immune response modifier |
| JP2007512349A (ja) * | 2003-11-25 | 2007-05-17 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドロキシルアミンおよびオキシム置換した、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 |
| WO2005055932A2 (en) * | 2003-12-02 | 2005-06-23 | 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 |
| AU2004315771A1 (en) * | 2003-12-04 | 2005-08-25 | 3M Innovative Properties Company | Sulfone substituted imidazo ring ethers |
| US8802853B2 (en) | 2003-12-29 | 2014-08-12 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| 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 |
| EP1699398A4 (en) * | 2003-12-30 | 2007-10-17 | 3M Innovative Properties Co | IMPROVING THE IMMUNE RESPONSE |
| WO2005066169A2 (en) | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| JP4991520B2 (ja) * | 2004-03-15 | 2012-08-01 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節剤製剤および方法 |
| AU2005228150A1 (en) | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| EP1735010A4 (en) * | 2004-04-09 | 2008-08-27 | 3M Innovative Properties Co | METHODS, COMPOSITIONS AND PREPARATIONS FOR ADMINISTRATION OF IMMUNE RESPONSE MODIFIERS (MRI) |
| CA2564855A1 (en) * | 2004-04-28 | 2005-10-28 | 3M Innovative Properties Company | Compositions and methods for mucosal vaccination |
| US20050267145A1 (en) * | 2004-05-28 | 2005-12-01 | Merrill Bryon A | Treatment for lung cancer |
| WO2005123079A2 (en) * | 2004-06-14 | 2005-12-29 | 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 |
| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| WO2006038923A2 (en) | 2004-06-18 | 2006-04-13 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| AU2005283085B2 (en) * | 2004-06-18 | 2012-06-21 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US20060045886A1 (en) * | 2004-08-27 | 2006-03-02 | Kedl Ross M | HIV immunostimulatory compositions |
| EP1799256A4 (en) * | 2004-08-27 | 2009-10-21 | 3M Innovative Properties Co | METHOD FOR PROVIDING AN IMMUNE RESPONSE AGAINST HIV |
| ATE555786T1 (de) * | 2004-09-02 | 2012-05-15 | 3M Innovative Properties Co | 1-alkoxy 1h-imidazo-ringsysteme und verfahren |
| US8143270B2 (en) | 2004-09-02 | 2012-03-27 | 3M Innovative Properties Company | 2-amino 1H-in-imidazo ring systems and methods |
| DE102004049223A1 (de) * | 2004-10-08 | 2006-04-20 | Johannes-Gutenberg-Universität Mainz | Zubereitung zum Impfen, Impfverfahren und Verwendung einer Impf-Zubereitung |
| US20070243215A1 (en) * | 2004-10-08 | 2007-10-18 | Miller Richard L | Adjuvant for Dna Vaccines |
| US9492400B2 (en) | 2004-11-04 | 2016-11-15 | Massachusetts Institute Of Technology | Coated controlled release polymer particles as efficient oral delivery vehicles for biopharmaceuticals |
| US8080560B2 (en) * | 2004-12-17 | 2011-12-20 | 3M Innovative Properties Company | Immune response modifier formulations containing oleic acid and methods |
| CA2592897A1 (en) * | 2004-12-30 | 2006-07-13 | Takeda Pharmaceutical Company Limited | 1-(2-methylpropyl)-1h-imidazo[4,5-c][1,5]naphthyridin-4-amine ethanesulfonate and 1-(2-methylpropyl)-1h-imidazo[4,5-c][1,5]naphthyridin-4-amine methanesulfonate |
| AU2005322898B2 (en) | 2004-12-30 | 2011-11-24 | 3M Innovative Properties Company | Chiral fused (1,2)imidazo(4,5-c) ring compounds |
| SI1830876T1 (sl) * | 2004-12-30 | 2015-08-31 | Meda Ab | Uporaba imikvimoda za zdravljenje kožnih metastaz, ki izhajajo iz rakavega tumorja dojke |
| 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 |
| JP5313502B2 (ja) | 2004-12-30 | 2013-10-09 | スリーエム イノベイティブ プロパティズ カンパニー | 置換キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| KR101415864B1 (ko) * | 2005-01-28 | 2014-07-09 | 갈렌바이오 인코포레이티드 | 면역학적 활성 조성물 |
| CA2597092A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| WO2006086449A2 (en) | 2005-02-09 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| JP2008530252A (ja) | 2005-02-09 | 2008-08-07 | 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 | オキシムおよびヒドロキシルアミンで置換されたチアゾロ［４，５−ｃ］環化合物ならびに方法 |
| AU2006216997A1 (en) | 2005-02-11 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Substituted imidazoquinolines and imidazonaphthyridines |
| CA2597587A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| WO2006091568A2 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazonaphthyridines |
| US8178677B2 (en) | 2005-02-23 | 2012-05-15 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
| US8158794B2 (en) | 2005-02-23 | 2012-04-17 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
| WO2006091647A2 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Method of preferentially inducing the biosynthesis of interferon |
| BRPI0608011A2 (pt) | 2005-03-14 | 2009-11-03 | Graceway Pharmaceuticals Llc | uso de uma formulação para o tratamento da queratose actìnica e uso de 2-metil-1-(2-metilpropil)-1h-imidazo[4,5-c][1,5] naftiridin-4-amina |
| EP1863814A1 (en) | 2005-04-01 | 2007-12-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| EP1869043A2 (en) | 2005-04-01 | 2007-12-26 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| AU2006241166A1 (en) * | 2005-04-25 | 2006-11-02 | 3M Innovative Properties Company | Immunostimulatory compositions |
| ES2577514T3 (es) * | 2005-08-22 | 2016-07-15 | The Regents Of The University Of California | Antagonistas de TLR |
| ZA200803029B (en) | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
| AU2006287270A1 (en) | 2005-09-09 | 2007-03-15 | Coley Pharmaceutical Group, Inc. | Amide and carbamate derivatives of N-{2-[4-amino-2- (ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide and methods |
| US8889154B2 (en) | 2005-09-15 | 2014-11-18 | Medicis Pharmaceutical Corporation | Packaging for 1-(2-methylpropyl)-1H-imidazo[4,5-c] quinolin-4-amine-containing formulation |
| ES2435775T3 (es) * | 2005-10-27 | 2013-12-23 | Janssen Biotech, Inc. | Moduladores de receptor tipo Toll 3, procedimientos y usos |
| ES2429170T3 (es) | 2005-11-04 | 2013-11-13 | 3M Innovative Properties Company | 1H-Imidazoquinolinas sustituidas con hidroxilo y alcoxilo y métodos |
| US9267937B2 (en) | 2005-12-15 | 2016-02-23 | Massachusetts Institute Of Technology | System for screening particles |
| WO2007079169A2 (en) * | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for acute myeloid leukemia |
| WO2007079171A2 (en) * | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for hodgkin's lymphoma |
| EP1968582A4 (en) * | 2005-12-28 | 2011-02-16 | 3M Innovative Properties Co | TREATMENT OF CUTTAN T CELL LYMPHOMA |
| WO2007079202A2 (en) * | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for acute lymhoblastic leukemia |
| WO2007079146A1 (en) * | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc | Treatment for non-hodgkin's lymphoma |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 3M Innovative Properties Company | Immune response modifier conjugates |
| US8329721B2 (en) | 2006-03-15 | 2012-12-11 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1H-imidazonaphthyridines and methods |
| ES2776100T3 (es) | 2006-03-31 | 2020-07-29 | Massachusetts Inst Technology | Sistema para el suministro dirigido de agentes terapéuticos |
| EP2019691B1 (en) | 2006-05-15 | 2020-08-12 | Massachusetts Institute of Technology | Polymers for functional particles |
| WO2007150030A2 (en) | 2006-06-23 | 2007-12-27 | Massachusetts Institute Of Technology | Microfluidic synthesis of organic nanoparticles |
| 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 |
| CN101240271B (zh) * | 2006-08-28 | 2012-08-29 | 长春华普生物技术有限公司 | Toll样受体调节性寡核苷酸及其用途 |
| 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 |
| EP2510946B1 (en) | 2007-02-07 | 2015-08-05 | The Regents of The University of California | Conjugates of synthetic tlr agonists and uses therefor |
| EP2134830A2 (en) | 2007-02-09 | 2009-12-23 | Massachusetts Institute of Technology | Oscillating cell culture bioreactor |
| US20090074828A1 (en) | 2007-04-04 | 2009-03-19 | Massachusetts Institute Of Technology | Poly(amino acid) targeting moieties |
| PL2155743T3 (pl) * | 2007-05-08 | 2013-01-31 | Astrazeneca Ab | Imidazochinoliny o właściwościach immunomodulacyjnych |
| MX350501B (es) | 2007-10-12 | 2017-09-07 | Massachusetts Inst Technology | Nanotecnologia de vacuna. |
| AU2009266940A1 (en) * | 2008-07-01 | 2010-01-07 | Emory University | Synergistic induction of humoral and cellular immunity by combinatorial activation of toll-like receptors |
| US8277812B2 (en) | 2008-10-12 | 2012-10-02 | Massachusetts Institute Of Technology | Immunonanotherapeutics that provide IgG humoral response without T-cell antigen |
| US8591905B2 (en) | 2008-10-12 | 2013-11-26 | The Brigham And Women's Hospital, Inc. | Nicotine immunonanotherapeutics |
| US8343498B2 (en) | 2008-10-12 | 2013-01-01 | Massachusetts Institute Of Technology | Adjuvant incorporation in immunonanotherapeutics |
| US8343497B2 (en) | 2008-10-12 | 2013-01-01 | The Brigham And Women's Hospital, Inc. | Targeting of antigen presenting cells with immunonanotherapeutics |
| CN102264394B (zh) * | 2008-10-24 | 2014-01-01 | 葛兰素史密丝克莱恩生物有限公司 | 脂化咪唑并喹啉衍生物 |
| WO2010088924A1 (en) | 2009-02-06 | 2010-08-12 | Telormedix Sa | Pharmaceutical compositions comprising imidazoquinolin(amines) and derivatives thereof suitable for local administration |
| AU2010229835B2 (en) | 2009-03-25 | 2015-01-15 | The Board Of Regents Of The University Of Texas System | Compositions for stimulation of mammalian innate immune resistance to pathogens |
| US9050319B2 (en) | 2010-04-30 | 2015-06-09 | Telormedix, Sa | Phospholipid drug analogs |
| WO2011134669A1 (en) * | 2010-04-30 | 2011-11-03 | Telormedix Sa | Methods for inducing an immune response |
| CN103221067B (zh) | 2010-04-30 | 2016-01-06 | 泰勒麦迪克斯公司 | 磷脂药物类似物 |
| EP2574170A4 (en) | 2010-05-10 | 2013-11-20 | Ascend Biopharmaceuticals Pty Ltd | IMMUNOSTIMULATORY AND VACCINE COMPOSITIONS |
| CN106177940A (zh) | 2010-05-26 | 2016-12-07 | 西莱克塔生物科技公司 | 含有佐剂的合成纳米载体的剂量选择 |
| EP3222621B1 (en) | 2010-08-17 | 2023-03-08 | 3M Innovative Properties Company | Lipidated immune response modifier compound and its medical use |
| US9994443B2 (en) | 2010-11-05 | 2018-06-12 | Selecta Biosciences, Inc. | Modified nicotinic compounds and related methods |
| EP3366311B1 (en) * | 2011-06-03 | 2020-02-26 | 3M Innovative Properties Co. | Hydrazino-1h-imidazoquinolin-4-amines and conjugates made therefrom |
| WO2012167088A1 (en) | 2011-06-03 | 2012-12-06 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| KR20140050698A (ko) | 2011-07-29 | 2014-04-29 | 셀렉타 바이오사이언시즈, 인크. | 체액성 및 세포독성 t 림프구(ctl) 면역 반응을 발생시키는 합성 나노운반체 |
| EP2941233B1 (en) | 2013-01-07 | 2020-10-07 | The Trustees of the University of Pennsylvania | Compositions and methods for treating cutaneous t cell lymphoma |
| GB201321242D0 (en) | 2013-12-02 | 2014-01-15 | Immune Targeting Systems Its Ltd | Immunogenic compound |
| US9695171B2 (en) | 2013-12-17 | 2017-07-04 | Pfizer Inc. | 3,4-disubstituted-1 H-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7H-pyrrolo[2,3-c]pyridazines as LRRK2 inhibitors |
| WO2016044839A2 (en) | 2014-09-19 | 2016-03-24 | The Board Of Regents Of The University Of Texas System | Compositions and methods for treating viral infections through stimulated innate immunity in combination with antiviral compounds |
| WO2016057618A1 (en) * | 2014-10-09 | 2016-04-14 | Wake Forest University Health Sciences | Vaccine compositions and methods of use to treat neonatal subjects |
| JP6873980B2 (ja) | 2015-09-14 | 2021-05-19 | ファイザー・インク | ＬＲＲＫ２阻害薬としての新規のイミダゾ［４，５−ｃ］キノリンおよびイミダゾ［４，５−ｃ］［１，５］ナフチリジン誘導体 |
| 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 |
| MA44334A (fr) | 2015-10-29 | 2018-09-05 | Novartis Ag | Conjugués d'anticorps comprenant un agoniste du récepteur de type toll |
| US11697851B2 (en) | 2016-05-24 | 2023-07-11 | The Regents Of The University Of California | Early ovarian cancer detection diagnostic test based on mRNA isoforms |
| EP3484518B1 (en) | 2016-07-07 | 2024-08-14 | The Board of Trustees of the Leland Stanford Junior University | Antibody adjuvant conjugates |
| ES2951817T3 (es) | 2017-08-22 | 2023-10-25 | Dynavax Tech Corp | Derivados de imidazoquinolina de cadena alquílica modificada como agonistas de TLR7/8 y usos de los mismos |
| 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 |
| CA3086439A1 (en) | 2017-12-20 | 2019-06-27 | 3M Innovative Properties Company | Amide substitued imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
| MX387358B (es) | 2018-02-28 | 2025-03-18 | Pfizer | Variantes de il-15 y usos de las mismas |
| CN108498362A (zh) * | 2018-04-17 | 2018-09-07 | 睿欧生物科技（上海）有限公司 | 预防及治疗口腔溃疡的Toll样受体激动剂漱口水 |
| MX2020012607A (es) | 2018-05-23 | 2021-01-29 | Pfizer | Anticuerpos especificos para gucy2c y sus usos. |
| EP3797121B1 (en) | 2018-05-23 | 2024-06-19 | Pfizer Inc. | Antibodies specific for cd3 and uses thereof |
| US20220370606A1 (en) | 2018-12-21 | 2022-11-24 | Pfizer Inc. | Combination Treatments Of Cancer Comprising A TLR Agonist |
| JP2022525594A (ja) | 2019-03-15 | 2022-05-18 | ボルト バイオセラピューティクス、インコーポレーテッド | Ｈｅｒ２を標的とする免疫結合体 |
| AU2020410410A1 (en) | 2019-12-17 | 2022-06-09 | Pfizer Inc. | Antibodies specific for CD47, PD-L1, and uses thereof |
| CA3161668A1 (en) * | 2019-12-20 | 2021-06-24 | Nammi Therapeutics, Inc. | Formulated and/or co-formulated liposome compositions containing toll-like receptor ("tlr") agonist prodrugs useful in the treatment of cancer and methods thereof |
| WO2021168274A1 (en) | 2020-02-21 | 2021-08-26 | Silverback Therapeutics, Inc. | Nectin-4 antibody conjugates and uses thereof |
| IL299508A (en) | 2020-07-01 | 2023-02-01 | Ars Pharmaceuticals Inc | Anti-asgr1 antibody conjugates and uses thereof |
| WO2022008995A1 (en) | 2020-07-08 | 2022-01-13 | 3M Innovative Properties Company | N-1 branched imidazoquinolines, conjugates thereof, and methods |
| BR112023000701A2 (pt) | 2020-07-17 | 2023-02-07 | Pfizer | Anticorpos terapêuticos e usos dos mesmos |
| WO2022031057A1 (ko) * | 2020-08-04 | 2022-02-10 | 성균관대학교산학협력단 | 활성화 부위가 일시적으로 비활성화된 톨-유사 수용체 7 또는 8 작용자와 기능성 약물의 결합체 및 그 용도 |
| US20230406855A1 (en) | 2020-12-16 | 2023-12-21 | 3M Innovative Properties Company | N-1 branched imidazoquinolines, conjugates thereof, and methods |
| CN118401523A (zh) | 2021-12-14 | 2024-07-26 | 舒万诺知识产权公司 | N-1三唑取代的咪唑并喹啉、其缀合物和方法 |
| WO2025104289A1 (en) | 2023-11-17 | 2025-05-22 | Medincell S.A. | Antineoplastic combinations |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000040228A2 (en) * | 1999-01-08 | 2000-07-13 | 3M Innovative Properties Company | Formulations comprising imiquimod or other immune response modifiers for treating mucosal conditions |
| WO2002046188A2 (en) * | 2000-12-08 | 2002-06-13 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
Family Cites Families (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL73534A (en) | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| 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 |
| JPH0832637B2 (ja) * | 1985-02-14 | 1996-03-29 | アクゾ・エヌ・ヴエー | 合成免疫原 |
| 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 |
| US4929624A (en) | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo(4,5-c)quinolin-4-amines |
| US5037986A (en) | 1989-03-23 | 1991-08-06 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo[4,5-c]quinolin-4-amines |
| NZ232740A (en) | 1989-04-20 | 1992-06-25 | Riker Laboratories Inc | Solution for parenteral administration comprising a 1h-imidazo(4,5-c) quinolin-4-amine derivative, an acid and a tonicity adjuster |
| US5350836A (en) * | 1989-10-12 | 1994-09-27 | Ohio University | Growth hormone antagonists |
| 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 |
| HU217080B (hu) | 1990-10-05 | 1999-11-29 | Minnesota Mining And Manufacturing Co. | Új eljárás imidazo[4,5-c]kinolin-4-amin-származékok előállítására |
| 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 |
| US5266575A (en) | 1991-11-06 | 1993-11-30 | Minnesota Mining And Manufacturing Company | 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines |
| IL105325A (en) | 1992-04-16 | 1996-11-14 | Minnesota Mining & Mfg | Immunogen/vaccine adjuvant composition |
| US5395937A (en) | 1993-01-29 | 1995-03-07 | Minnesota Mining And Manufacturing Company | Process for preparing quinoline amines |
| EP0622681B1 (en) | 1993-04-27 | 1997-10-01 | Agfa-Gevaert N.V. | Process for incorporation of a water-insoluble substance into a hydrophilic layer |
| US5352784A (en) | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| EP0708772B1 (en) | 1993-07-15 | 2000-08-23 | Minnesota Mining And Manufacturing Company | IMIDAZO [4,5-c]PYRIDIN-4-AMINES |
| US6207646B1 (en) | 1994-07-15 | 2001-03-27 | University Of Iowa Research Foundation | Immunostimulatory nucleic acid molecules |
| DK0772619T4 (da) | 1994-07-15 | 2011-02-21 | Univ Iowa Res Found | Immunmodulatoriske oligonukleotider |
| US6239116B1 (en) | 1994-07-15 | 2001-05-29 | University Of Iowa Research Foundation | Immunostimulatory nucleic acid molecules |
| US5521289A (en) | 1994-07-29 | 1996-05-28 | Nanoprobes, Inc. | Small organometallic probes |
| US5482936A (en) | 1995-01-12 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-C]quinoline amines |
| 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 |
| 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 |
| ATE283855T1 (de) | 1996-07-03 | 2004-12-15 | Sumitomo Pharma | Neue purinderivate |
| US6387938B1 (en) | 1996-07-05 | 2002-05-14 | Mochida Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| US6610661B1 (en) * | 1996-10-11 | 2003-08-26 | The Regents Of The University Of California | Immunostimulatory polynucleotide/immunomodulatory molecule conjugates |
| US6039969A (en) | 1996-10-25 | 2000-03-21 | 3M Innovative Properties Company | Immune response modifier compounds for treatment of TH2 mediated and related diseases |
| US5939090A (en) | 1996-12-03 | 1999-08-17 | 3M Innovative Properties Company | Gel formulations for topical drug delivery |
| WO1998026747A2 (en) | 1996-12-17 | 1998-06-25 | Terman David S | Superantigen based methods and compositions for treatment of diseases |
| EP0894797A4 (en) | 1997-01-09 | 2001-08-16 | Terumo Corp | NEW AMID DERIVATIVES AND INTERMEDIATES ON YOUR SYNTHESIS |
| US6800746B2 (en) * | 1997-02-25 | 2004-10-05 | Corixa Corporation | Compositions and methods for the therapy and diagnosis of prostate cancer |
| US6406705B1 (en) | 1997-03-10 | 2002-06-18 | University Of Iowa Research Foundation | Use of nucleic acids containing unmethylated CpG dinucleotide as an adjuvant |
| US6426334B1 (en) | 1997-04-30 | 2002-07-30 | Hybridon, Inc. | Oligonucleotide mediated specific cytokine induction and reduction of tumor growth in a mammal |
| DE69838294T2 (de) | 1997-05-20 | 2009-08-13 | Ottawa Health Research Institute, Ottawa | Verfahren zur Herstellung von Nukleinsäurekonstrukten |
| JPH1180156A (ja) | 1997-09-04 | 1999-03-26 | Hokuriku Seiyaku Co Ltd | １−（置換アリール）アルキル−１ｈ−イミダゾピリジン−４−アミン誘導体 |
| US6329381B1 (en) | 1997-11-28 | 2001-12-11 | Sumitomo Pharmaceuticals Company, Limited | Heterocyclic compounds |
| UA67760C2 (uk) | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
| TW572758B (en) | 1997-12-22 | 2004-01-21 | Sumitomo Pharma | Type 2 helper T cell-selective immune response inhibitors comprising purine derivatives |
| JPH11222432A (ja) | 1998-02-03 | 1999-08-17 | Terumo Corp | インターフェロンを誘起するアミド誘導体を含有する外用剤 |
| FR2775622A1 (fr) | 1998-03-03 | 1999-09-03 | Atochem Elf Sa | Catalyseur bimetallique supporte a base de platine ou d'argent, son procede de fabrication et son utilisation pour les cellules electrochimiques |
| AU760669B2 (en) * | 1998-04-28 | 2003-05-22 | Galenica Pharmaceuticals, Inc. | Polysaccharide-antigen conjugates |
| US6110929A (en) | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| JP2000119271A (ja) | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | １ｈ―イミダゾピリジン誘導体 |
| US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| 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 |
| AU776268B2 (en) | 1999-06-08 | 2004-09-02 | Aventis Pasteur | Immunostimulant oligonucleotide |
| US6331539B1 (en) | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide 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 |
| CA2381993A1 (en) | 1999-08-13 | 2001-02-22 | Hybridon, Inc. | Modulation of oligonucleotide cpg-mediated immune stimulation by positional modification of nucleosides |
| US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| US20040023870A1 (en) | 2000-01-21 | 2004-02-05 | Douglas Dedera | Methods of therapy and diagnosis using targeting of cells that express toll-like receptor proteins |
| GB0001704D0 (en) | 2000-01-25 | 2000-03-15 | Glaxo Group Ltd | Protein |
| AU2001245823A1 (en) * | 2000-03-17 | 2001-10-03 | Corixa Corporation | Novel amphipathic aldehydes and their use as adjuvants and immunoeffectors |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| DE10036282A1 (de) | 2000-07-26 | 2002-02-07 | Bosch Gmbh Robert | Verfahren und Vorrichtung zur Steuerung einer Antriebseinheit |
| US20020055517A1 (en) | 2000-09-15 | 2002-05-09 | 3M Innovative Properties Company | Methods for delaying recurrence of herpes virus symptoms |
| GB0023008D0 (en) * | 2000-09-20 | 2000-11-01 | Glaxo Group Ltd | Improvements in vaccination |
| 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 |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| US6660747B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| UA74593C2 (en) | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
| AU3249802A (en) | 2000-12-08 | 2002-06-18 | 3M Innovative Properties Co | Screening method for identifying compounds that selectively induce interferon alpha |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US7157465B2 (en) | 2001-04-17 | 2007-01-02 | Dainippon Simitomo Pharma Co., Ltd. | Adenine derivatives |
| WO2002102377A1 (en) | 2001-06-15 | 2002-12-27 | 3M Innovative Properties Company | Immune response modifiers for the treatment of periodontal disease |
| MXPA04001972A (es) | 2001-08-30 | 2005-02-17 | 3M Innovative Properties Co | Metodos para hacer madurar celulas dendricas plasmacitoide utilizando moleculas modificadoras de respuesta enmune. |
| EP1478371A4 (en) * | 2001-10-12 | 2007-11-07 | Univ Iowa Res Found | METHOD AND PRODUCTS FOR IMPROVING IMMUNE RESPONSES WITH IMIDAZOCHINOLINE COMPOUNDS |
| EP1719511B1 (en) | 2001-11-16 | 2008-12-10 | 3M Innovative Properties Company | N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide, a pharmaceutical composition comprising the same and use thereof |
| NZ532769A (en) | 2001-11-29 | 2005-12-23 | 3M Innovative Properties Co | Pharmaceutical formulations comprising an immune response modifier |
| US7501134B2 (en) * | 2002-02-20 | 2009-03-10 | Novartis Vaccines And Diagnostics, Inc. | Microparticles with adsorbed polypeptide-containing molecules |
| SI1478327T1 (sl) | 2002-02-22 | 2015-08-31 | Meda Ab | Metoda za zmanjšanje in zdravljenje imunosupresije, inducirane z UV-B |
| ES2543710T3 (es) | 2002-04-04 | 2015-08-21 | Zoetis Belgium S.A. | Oligorribonucleótidos inmunoestimulantes que contienen G y U |
| AU2003225054A1 (en) | 2002-04-19 | 2003-11-03 | Yale University | Toll-like receptor 11 and toll-like receptor 12 |
| WO2005018555A2 (en) * | 2003-08-14 | 2005-03-03 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
-
2003
- 2003-08-14 EP EP03808061A patent/EP1545597B1/en not_active Expired - Lifetime
- 2003-08-14 EP EP10181530.6A patent/EP2269632B1/en not_active Expired - Lifetime
- 2003-08-14 CA CA2495570A patent/CA2495570C/en not_active Expired - Fee Related
- 2003-08-14 US US10/640,904 patent/US7427629B2/en not_active Expired - Fee Related
- 2003-08-14 CN CN038184702A patent/CN1671412B/zh not_active Expired - Fee Related
- 2003-08-14 AU AU2003299863A patent/AU2003299863B2/en not_active Ceased
- 2003-08-14 ES ES03808061T patent/ES2355819T3/es not_active Expired - Lifetime
- 2003-08-14 WO PCT/US2003/025523 patent/WO2004032829A2/en not_active Ceased
- 2003-08-14 NZ NZ538812A patent/NZ538812A/en not_active IP Right Cessation
- 2003-08-14 AT AT03808061T patent/ATE488246T1/de active
- 2003-08-14 BR BRPI0313587-0A patent/BR0313587A/pt not_active IP Right Cessation
- 2003-08-14 JP JP2004543241A patent/JP4860923B2/ja not_active Expired - Fee Related
- 2003-08-14 MX MXPA05001647A patent/MXPA05001647A/es active IP Right Grant
- 2003-08-14 KR KR1020057002485A patent/KR101088615B1/ko not_active Expired - Fee Related
- 2003-08-14 DK DK03808061.0T patent/DK1545597T3/da active
- 2003-08-14 DE DE60335010T patent/DE60335010D1/de not_active Expired - Lifetime
- 2003-08-14 PT PT03808061T patent/PT1545597E/pt unknown
-
2010
- 2010-11-22 JP JP2010260166A patent/JP5491364B2/ja not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000040228A2 (en) * | 1999-01-08 | 2000-07-13 | 3M Innovative Properties Company | Formulations comprising imiquimod or other immune response modifiers for treating mucosal conditions |
| WO2002046188A2 (en) * | 2000-12-08 | 2002-06-13 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| WO2002046189A2 (en) * | 2000-12-08 | 2002-06-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
Non-Patent Citations (2)
| Title |
|---|
| Vasilakos, J.P. et al. Cell. Immunol. 2000, vol. 204, pp. 64-74. * |
| Wagner, T.L. et al. Cell. Immunol. 1999, vol. 191, pp. 10-19. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2495570A1 (en) | 2004-04-22 |
| US7427629B2 (en) | 2008-09-23 |
| KR101088615B1 (ko) | 2011-11-30 |
| DE60335010D1 (de) | 2010-12-30 |
| DK1545597T3 (da) | 2011-01-31 |
| NZ538812A (en) | 2009-02-28 |
| EP1545597A4 (en) | 2006-08-30 |
| JP4860923B2 (ja) | 2012-01-25 |
| JP2011057699A (ja) | 2011-03-24 |
| AU2003299863A2 (en) | 2004-05-04 |
| KR20050026709A (ko) | 2005-03-15 |
| US20040091491A1 (en) | 2004-05-13 |
| EP2269632B1 (en) | 2014-01-01 |
| WO2004032829A3 (en) | 2004-12-09 |
| WO2004032829A2 (en) | 2004-04-22 |
| EP2269632A2 (en) | 2011-01-05 |
| PT1545597E (pt) | 2010-12-29 |
| CN1671412A (zh) | 2005-09-21 |
| MXPA05001647A (es) | 2005-04-19 |
| JP2006507265A (ja) | 2006-03-02 |
| CA2495570C (en) | 2012-12-04 |
| ES2355819T3 (es) | 2011-03-31 |
| BR0313587A (pt) | 2006-06-13 |
| ATE488246T1 (de) | 2010-12-15 |
| JP5491364B2 (ja) | 2014-05-14 |
| EP1545597B1 (en) | 2010-11-17 |
| EP2269632A3 (en) | 2012-10-24 |
| EP1545597A2 (en) | 2005-06-29 |
| CN1671412B (zh) | 2010-05-26 |
| AU2003299863A1 (en) | 2004-05-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2003299863B2 (en) | Immunostimulatory compositions and methods of stimulating an immune response | |
| US10472420B2 (en) | Immune response modifier conjugates | |
| US20060045885A1 (en) | Method of eliciting an immune response against HIV | |
| EP2717919B1 (en) | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom | |
| AU2005244260B2 (en) | Methods, compositions, and preparations for delivery of immune response modifiers | |
| EP3366311B1 (en) | Hydrazino-1h-imidazoquinolin-4-amines and conjugates made therefrom | |
| US20060045886A1 (en) | HIV immunostimulatory compositions | |
| JP2014532799A (ja) | 免疫調節結合体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 14 MAR 2005 |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |