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)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Communicable Diseases (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)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (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)
Families Citing this family (155)
| 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 |
| 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 |
| 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 |
| JP2008531580A (ja) * | 2000-12-08 | 2008-08-14 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答修飾因子の標的化送達のための組成物および方法 |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US6677349B1 (en) * | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| EP1478327B1 (en) * | 2002-02-22 | 2015-04-29 | Meda AB | Method of reducing and treating uvb-induced immunosuppression |
| NZ535952A (en) | 2002-04-04 | 2009-01-31 | Coley Pharm Gmbh | Immunostimulatory G,U-containing oligoribonucleotides |
| EP1513524A4 (en) | 2002-06-07 | 2008-09-03 | 3M Innovative Properties Co | WITH ETHER SUBSTITUTED IMIDAZOPYRIDINE |
| US7091214B2 (en) | 2002-12-20 | 2006-08-15 | 3M Innovative Properties Co. | Aryl substituted Imidazoquinolines |
| US8426457B2 (en) * | 2003-03-13 | 2013-04-23 | Medicis Pharmaceutical Corporation | Methods of improving skin quality |
| 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 |
| CA2521662A1 (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 |
| AR044466A1 (es) * | 2003-06-06 | 2005-09-14 | 3M Innovative Properties Co | Proceso para la preparacion de imidazo [4,5-c] piridin-4-aminas |
| CN1852711A (zh) * | 2003-08-05 | 2006-10-25 | 3M创新有限公司 | 使用免疫响应调节化合物的传染病预防 |
| BRPI0412902A (pt) | 2003-08-12 | 2006-09-26 | 3M Innovative Properties Co | compostos contendo imidazo substituìdo por oxima |
| EP2939693A1 (en) * | 2003-08-14 | 2015-11-04 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
| AU2004268616B2 (en) * | 2003-08-25 | 2010-10-07 | 3M Innovative Properties Company | Delivery of immune response modifier compounds |
| JP2007504145A (ja) * | 2003-08-25 | 2007-03-01 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫刺激性の組み合わせおよび治療 |
| CA2536136C (en) | 2003-08-27 | 2012-10-30 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| AU2004270201A1 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for CD5+ B cell lymphoma |
| US20050059072A1 (en) * | 2003-09-17 | 2005-03-17 | 3M Innovative Properties Company | Selective modulation of TLR gene expression |
| CA2540541C (en) | 2003-10-03 | 2012-03-27 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| NZ546274A (en) | 2003-10-03 | 2009-12-24 | 3M Innovative Properties Co | Pyrazolopyridines and analags thereof |
| US7544697B2 (en) * | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| US20050096259A1 (en) * | 2003-10-31 | 2005-05-05 | 3M Innovative Properties Company | Neutrophil activation by immune response modifier compounds |
| WO2005048933A2 (en) * | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
| US8598192B2 (en) | 2003-11-14 | 2013-12-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazoquinolines |
| WO2005051324A2 (en) * | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| AU2004293078B2 (en) | 2003-11-25 | 2012-01-19 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| JP2007513165A (ja) * | 2003-12-02 | 2007-05-24 | スリーエム イノベイティブ プロパティズ カンパニー | Ｉｒｍ化合物を含む併用薬および治療方法 |
| US20050226878A1 (en) * | 2003-12-02 | 2005-10-13 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
| TW200533352A (en) * | 2003-12-04 | 2005-10-16 | 3M Innovative Properties Co | Sulfone substituted imidazo ring ethers |
| EP1701955A1 (en) | 2003-12-29 | 2006-09-20 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| CN1922178A (zh) * | 2003-12-29 | 2007-02-28 | 3M创新有限公司 | 哌嗪、[1, 4 ]二氮杂环庚烷([1,4]diazepane ) 、[1, 4 ]二氮杂环辛烷([1, 4]diazocane)、和[1,5]二氮杂环辛烷([1,5] diazocane) 稠合的咪唑并环化合物 |
| 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 |
| ES2665342T3 (es) * | 2004-03-15 | 2018-04-25 | Meda Ab | Formulaciones y métodos para modificadores de la respuesta inmune |
| CA2559863A1 (en) | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005110013A2 (en) * | 2004-04-09 | 2005-11-24 | 3M Innovative Properties Company | Methods, compositions, and preparations for delivery of immune response modifiers |
| MXPA06012451A (es) * | 2004-04-28 | 2007-01-31 | 3M Innovative Properties Co | Composiciones y metodos para vacunacion por la mucosa. |
| US20050267145A1 (en) * | 2004-05-28 | 2005-12-01 | Merrill Bryon A | Treatment for lung cancer |
| US20080015184A1 (en) * | 2004-06-14 | 2008-01-17 | 3M Innovative Properties Company | Urea Substituted Imidazopyridines, Imidazoquinolines, and Imidazonaphthyridines |
| WO2005123080A2 (en) | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| AU2005283085B2 (en) * | 2004-06-18 | 2012-06-21 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US7915281B2 (en) | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| 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 |
| WO2006026470A2 (en) * | 2004-08-27 | 2006-03-09 | 3M Innovative Properties Company | Hiv immunostimulatory compositions |
| WO2006026394A2 (en) * | 2004-08-27 | 2006-03-09 | 3M Innovative Properties Company | Method of eliciting an immune response against hiv |
| EP1784180A4 (en) | 2004-09-02 | 2009-07-22 | 3M Innovative Properties Co | 2-AMINO-1H-IMIDAZO RING SYSTEMS AND METHOD |
| ES2384390T3 (es) * | 2004-09-02 | 2012-07-04 | 3M Innovative Properties Company | Sistemas cíclicos 1-alcoxi-1H-imidazo y métodos asociados |
| DE102004049223A1 (de) * | 2004-10-08 | 2006-04-20 | Johannes-Gutenberg-Universität Mainz | Zubereitung zum Impfen, Impfverfahren und Verwendung einer Impf-Zubereitung |
| JP2008515928A (ja) * | 2004-10-08 | 2008-05-15 | スリーエム イノベイティブ プロパティズ カンパニー | Ｄｎａワクチンのためのアジュバント |
| WO2007001448A2 (en) | 2004-11-04 | 2007-01-04 | 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 |
| US7943609B2 (en) | 2004-12-30 | 2011-05-17 | 3M Innovative Proprerties Company | Chiral fused [1,2]imidazo[4,5-C] ring compounds |
| ES2392648T3 (es) | 2004-12-30 | 2012-12-12 | 3M Innovative Properties Company | Compuestos quirales sustituidos que contienen un núcleo 1,2-imidazo-4,5-c condensado |
| JP2008526751A (ja) * | 2004-12-30 | 2008-07-24 | 武田薬品工業株式会社 | １−（２−メチルプロピル）−１ｈ−イミダゾ［４，５−ｃ］［１，５］ナフチリジン−４−アミンエタンスルホナート及び１−（２−メチルプロピル）−１ｈ−イミダゾ［４，５−ｃ］［１，５］ナフチリジン−４−アミンメタンスルホナート |
| 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 |
| CA2594253C (en) * | 2004-12-30 | 2015-08-11 | 3M Innovative Properties Company | Treatment for cutaneous metastases |
| CA2606349C (en) * | 2005-01-28 | 2019-03-05 | Galen Bio, Inc. | Immunologically active compositions |
| US9248127B2 (en) | 2005-02-04 | 2016-02-02 | 3M Innovative Properties Company | Aqueous gel formulations containing immune response modifiers |
| US20080318998A1 (en) | 2005-02-09 | 2008-12-25 | Coley Pharmaceutical Group, Inc. | Alkyloxy Substituted Thiazoloquinolines and Thiazolonaphthyridines |
| WO2007120121A2 (en) | 2005-02-09 | 2007-10-25 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazolo[4,5-c] ring compounds and methods |
| WO2006091394A2 (en) | 2005-02-11 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Substituted imidazoquinolines and imidazonaphthyridines |
| EP1846405A2 (en) | 2005-02-11 | 2007-10-24 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted imidazo 4,5-c ring compounds and methods |
| CA2598437A1 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Method of preferentially inducing the biosynthesis of interferon |
| CA2598656A1 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
| EP1851224A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
| JP2008531568A (ja) | 2005-02-23 | 2008-08-14 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ヒドロキシアルキルで置換されたイミダゾナフチリジン |
| RU2007137960A (ru) | 2005-03-14 | 2009-04-20 | Меда Аб (Se) | СПОСОБ ЛЕЧЕНИЯ АКТИНИЧЕСКОГО КЕРАТОЗА (ВАРИАНТЫ) И 2-МЕТИЛ-1-(2-МЕТИЛПРОПИЛ)-1Н-ИМИДАЗО[4,5-c]]1,5]НАФТИРИДИН-4-АМИН В КАЧЕСТВЕ СРЕДСТВА ЛЕЧЕНИЯ АКТИНИЧЕСКОГО КЕРАТОЗА |
| AU2006232377A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| CA2602590A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| US20080193474A1 (en) * | 2005-04-25 | 2008-08-14 | Griesgraber George W | Immunostimulatory Compositions |
| JP2009504803A (ja) * | 2005-08-22 | 2009-02-05 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | Ｔｌｒアゴニスト |
| EP1922317A4 (en) | 2005-09-09 | 2009-04-15 | Coley Pharm Group Inc | N- {2-Ý4-AMINO-2- (ETHOXYMETHYL) -1H-IMIDAZOÝ4,5-CQUINOLIN-1-YL-1,1-DIMETHYLTHYL} METHANESULFONAMIDE AMIDE AND CARBAMATE DERIVATIVES AND RELATED METHODS |
| ZA200803029B (en) | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
| US8889154B2 (en) | 2005-09-15 | 2014-11-18 | Medicis Pharmaceutical Corporation | Packaging for 1-(2-methylpropyl)-1H-imidazo[4,5-c] quinolin-4-amine-containing formulation |
| JP5199878B2 (ja) * | 2005-10-27 | 2013-05-15 | セントカー・インコーポレーテツド | Ｔｏｌｌ様受容体３モジュレーター、方法および用途 |
| AU2006311871B2 (en) | 2005-11-04 | 2011-03-03 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1H-imidazoquinolines and methods |
| US9267937B2 (en) | 2005-12-15 | 2016-02-23 | Massachusetts Institute Of Technology | System for screening particles |
| 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 |
| WO2007079171A2 (en) * | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for hodgkin's lymphoma |
| WO2007079203A2 (en) * | 2005-12-28 | 2007-07-12 | 3M Innovative Properties Company | Treatment for cutaneous t cell lymphoma |
| WO2007079169A2 (en) * | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for acute myeloid leukemia |
| EP1988896A4 (en) * | 2006-02-22 | 2011-07-27 | 3M Innovative Properties Co | CONJUGATES TO MODIFY IMMUNE REACTIONS |
| US8329721B2 (en) | 2006-03-15 | 2012-12-11 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1H-imidazonaphthyridines and methods |
| JP2009534309A (ja) | 2006-03-31 | 2009-09-24 | マサチューセッツ インスティテュート オブ テクノロジー | 治療剤の標的化送達のためのシステム |
| JP5630998B2 (ja) | 2006-05-15 | 2014-11-26 | マサチューセッツ インスティテュート オブ テクノロジー | 機能的粒子のためのポリマー |
| 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 |
| CN102851295B (zh) * | 2006-08-28 | 2015-01-07 | 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 |
| PL2125007T3 (pl) | 2007-02-07 | 2014-07-31 | Univ California | Koniugaty syntetycznych agonistów TLR i ich zastosowania |
| WO2008098165A2 (en) | 2007-02-09 | 2008-08-14 | Massachusetts Institute Of Technology | Oscillating cell culture bioreactor |
| JP2010523595A (ja) | 2007-04-04 | 2010-07-15 | マサチューセッツ インスティテュート オブ テクノロジー | ポリ（アミノ酸）ターゲッティング部分 |
| PL2155743T3 (pl) * | 2007-05-08 | 2013-01-31 | Astrazeneca Ab | Imidazochinoliny o właściwościach immunomodulacyjnych |
| US10736848B2 (en) | 2007-10-12 | 2020-08-11 | Massachusetts Institute Of Technology | Vaccine nanotechnology |
| WO2010003009A2 (en) * | 2008-07-01 | 2010-01-07 | Emory University | Synergistic induction of humoral and cellular immunity by combinatorial activation of toll-like receptors |
| US8343497B2 (en) | 2008-10-12 | 2013-01-01 | The Brigham And Women's Hospital, Inc. | Targeting of antigen presenting cells with immunonanotherapeutics |
| US8591905B2 (en) | 2008-10-12 | 2013-11-26 | The Brigham And Women's Hospital, Inc. | Nicotine immunonanotherapeutics |
| US8277812B2 (en) | 2008-10-12 | 2012-10-02 | Massachusetts Institute Of Technology | Immunonanotherapeutics that provide IgG humoral response without T-cell antigen |
| US8343498B2 (en) | 2008-10-12 | 2013-01-01 | Massachusetts Institute Of Technology | Adjuvant incorporation in immunonanotherapeutics |
| BRPI0919937A2 (pt) | 2008-10-24 | 2016-02-16 | Glaxosmithkline Biolog Sa | composto, e, método para melhorar a atividade de adjuvante de uma imidazoquinolina |
| 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 |
| WO2011134668A1 (en) * | 2010-04-30 | 2011-11-03 | Telormedix Sa | Phospholipid drug analogs |
| US9050319B2 (en) | 2010-04-30 | 2015-06-09 | Telormedix, Sa | Phospholipid drug analogs |
| EP2563401A1 (en) * | 2010-04-30 | 2013-03-06 | Telormedix SA | Methods for inducing an immune response |
| US9597392B2 (en) | 2010-05-10 | 2017-03-21 | Ascend Biopharmaceuticals Pty Ltd. | Use of high molecular weight mannan for inducing and/or enhancing an immune response |
| US20110293700A1 (en) | 2010-05-26 | 2011-12-01 | Selecta Biosciences, Inc. | Nanocarrier compositions with uncoupled adjuvant |
| LT2606047T (lt) | 2010-08-17 | 2017-04-10 | 3M Innovative Properties Company | Imuninio atsako modifikatoriaus junginio lipidizuotos kompozicijos, sudėtys ir būdai |
| WO2012061717A1 (en) | 2010-11-05 | 2012-05-10 | Selecta Biosciences, Inc. | Modified nicotinic compounds and related methods |
| CN103582496B (zh) * | 2011-06-03 | 2016-05-11 | 3M创新有限公司 | 具有聚乙二醇链段的异双官能连接基以及由其制成的免疫应答调节剂缀合物 |
| AU2012261959B2 (en) * | 2011-06-03 | 2015-12-03 | Solventum Intellectual Properties Company | Hydrazino 1H-imidazoquinolin-4-amines and conjugates made therefrom |
| EP2736537A4 (en) | 2011-07-29 | 2015-04-15 | Selecta Biosciences Inc | SYNTHETIC NANOTRANSPORTERS FOR THE PRODUCTION OF HUMOROUS AND CYTOTOXIC T-LYMPHOCY (CTL) IMMUNE REACTIONS |
| EP3756669A1 (en) | 2013-01-07 | 2020-12-30 | The Trustees of the University of Pennsylvania | Compositions for use for treating cutaneous t cell lymphoma |
| GB201321242D0 (en) | 2013-12-02 | 2014-01-15 | Immune Targeting Systems Its Ltd | Immunogenic compound |
| JP6487921B2 (ja) | 2013-12-17 | 2019-03-20 | ファイザー・インク | ＬＲＲＫ２阻害薬としての新規の３，４−二置換−１Ｈ−ピロロ［２，３−ｂ］ピリジンおよび４，５−二置換−７Ｈ−ピロロ［２，３−ｃ］ピリダジン |
| US10286065B2 (en) | 2014-09-19 | 2019-05-14 | Board Of Regents, 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 |
| WO2017046675A1 (en) | 2015-09-14 | 2017-03-23 | Pfizer Inc. | Novel imidazo [4,5-c] quinoline and imidazo [4,5-c][1,5] naphthyridine derivatives as lrrk2 inhibitors |
| 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 |
| WO2018009916A1 (en) | 2016-07-07 | 2018-01-11 | The Board Of Trustees Of The Leland Stanford Junior University | Antibody adjuvant conjugates |
| JP7386536B2 (ja) | 2017-08-22 | 2023-11-27 | ダイナヴァックス テクノロジーズ コーポレイション | アルキル鎖修飾イミダゾキノリンｔｌｒ７／８アゴニスト化合物およびその使用 |
| EP3710059A1 (en) | 2017-11-14 | 2020-09-23 | Dynavax Technologies Corporation | Cleavable conjugates of tlr7/8 agonist compounds, methods for preparation, and uses thereof |
| JP7197244B2 (ja) | 2017-12-20 | 2022-12-27 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節剤として使用するための分岐鎖連結基を有するアミド置換イミダゾ［４，５－ｃ］キノリン化合物 |
| JP2021516045A (ja) | 2018-02-28 | 2021-07-01 | ファイザー・インク | Ｉｌ−１５バリアントおよびその使用 |
| 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 |
| TWI803637B (zh) | 2018-05-23 | 2023-06-01 | 美商輝瑞大藥廠 | 特異性針對gucy2c之抗體及其用途 |
| AU2019274654B2 (en) | 2018-05-23 | 2023-07-20 | 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 |
| EP3937984A1 (en) | 2019-03-15 | 2022-01-19 | Bolt Biotherapeutics, Inc. | Immunoconjugates targeting her2 |
| WO2021124073A1 (en) | 2019-12-17 | 2021-06-24 | Pfizer Inc. | Antibodies specific for cd47, pd-l1, and uses thereof |
| CN114901275A (zh) * | 2019-12-20 | 2022-08-12 | 纳米医疗有限公司 | 可用于治疗癌症的含有Toll样受体(“TLR”)激动剂前药的配制和/或共同配制的脂质体组合物及其方法 |
| WO2021168274A1 (en) | 2020-02-21 | 2021-08-26 | Silverback Therapeutics, Inc. | Nectin-4 antibody conjugates and uses thereof |
| CN116209678A (zh) | 2020-07-01 | 2023-06-02 | 安尔士制药公司 | 抗asgr1抗体缀合物及其用途 |
| JP2023533011A (ja) | 2020-07-08 | 2023-08-01 | スリーエム イノベイティブ プロパティズ カンパニー | Ｎ－１分岐イミダゾキノリン、そのコンジュゲート、及び方法 |
| TW202216779A (zh) | 2020-07-17 | 2022-05-01 | 美商輝瑞股份有限公司 | 治療性抗體類和彼等之用途 |
| EP4194010A1 (en) * | 2020-08-04 | 2023-06-14 | Progeneer Inc. | Conjugate of functional drug and toll-like receptor 7 or 8 agonist of which active site is temporarily inactivated and use thereof |
| JP2023554377A (ja) | 2020-12-16 | 2023-12-27 | スリーエム イノベイティブ プロパティズ カンパニー | Ｎ－１分岐イミダゾキノリン、そのコンジュゲート、及び方法 |
| WO2023111726A1 (en) | 2021-12-14 | 2023-06-22 | 3M Innovative Properties Company | N-1 triazole substituted imidazoquinolines, conjugates thereof, and methods |
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 |
| WO2002046189A2 (en) * | 2000-12-08 | 2002-06-13 | 3M Innovative Properties Company | Aryl 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 |
| CA1267087A (en) * | 1985-02-14 | 1990-03-27 | Nicolaas Visser | Synthetic immunogen |
| US5238944A (en) | 1988-12-15 | 1993-08-24 | Riker Laboratories, Inc. | Topical formulations and transdermal delivery systems containing 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine |
| US5756747A (en) | 1989-02-27 | 1998-05-26 | Riker Laboratories, Inc. | 1H-imidazo 4,5-c!quinolin-4-amines |
| US5037986A (en) | 1989-03-23 | 1991-08-06 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo[4,5-c]quinolin-4-amines |
| US4929624A (en) | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo(4,5-c)quinolin-4-amines |
| NZ232740A (en) | 1989-04-20 | 1992-06-25 | Riker Laboratories Inc | Solution for parenteral administration comprising a 1h-imidazo(4,5-c) quinolin-4-amine derivative, an acid and a tonicity adjuster |
| 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 |
| DE69108920T2 (de) | 1990-10-05 | 1995-11-30 | Minnesota Mining & Mfg | Verfahren zur herstellung von imidazo[4,5-c]chinolin-4-aminen. |
| 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 |
| US6239116B1 (en) | 1994-07-15 | 2001-05-29 | University Of Iowa Research Foundation | Immunostimulatory nucleic acid molecules |
| EP1167379A3 (en) | 1994-07-15 | 2004-09-08 | University Of Iowa Research Foundation | Immunomodulatory oligonucleotides |
| 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 |
| DE69731823T2 (de) | 1996-07-03 | 2005-12-15 | Sumitomo Pharmaceuticals Co., Ltd. | Neue purinderivate |
| US6387938B1 (en) | 1996-07-05 | 2002-05-14 | Mochida Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| EP1537877A3 (en) * | 1996-10-11 | 2005-08-03 | The Regents Of The University Of California | Immunostimulatory polynucleotide/immunomodulatory molecule conjugates |
| KR100518903B1 (ko) | 1996-10-25 | 2005-10-06 | 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 | Ｔｈ2 매개 질병 및 관련 질병의 치료용 면역 반응 조절 화합물 |
| 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 |
| US6339068B1 (en) | 1997-05-20 | 2002-01-15 | University Of Iowa Research Foundation | Vectors and methods for immunization or therapeutic protocols |
| 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 |
| US6573245B1 (en) * | 1998-04-28 | 2003-06-03 | Galenica Pharmaceuticals, Inc. | Modified polysaccharide adjuvant-protein antigen conjugates, the preparation thereof and the use thereof |
| 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 |
| WO2000075304A1 (fr) | 1999-06-08 | 2000-12-14 | Aventis Pasteur | Oligonucleotide immunostimulant |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6451810B1 (en) | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6331539B1 (en) | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| JP5268214B2 (ja) | 1999-08-13 | 2013-08-21 | イデラ ファーマシューティカルズ インコーポレイテッド | ヌクレオシドの位置的修飾によるオリゴヌクレオチドＣｐＧ−媒体免疫刺激の変調 |
| 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 |
| WO2001070663A2 (en) * | 2000-03-17 | 2001-09-27 | 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 |
| UA74593C2 (en) | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
| JP2005500510A (ja) | 2000-12-08 | 2005-01-06 | スリーエム イノベイティブ プロパティズ カンパニー | インターフェロンαを選択的に誘導する化合物を同定するための選別法 |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| US6660747B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| EP1386923B1 (en) | 2001-04-17 | 2008-08-13 | Dainippon Sumitomo Pharma Co., Ltd. | Novel adenine derivatives |
| CN1523987A (zh) | 2001-06-15 | 2004-08-25 | 3M创新有限公司 | 治疗牙周疾病的免疫反应调节剂 |
| US20030133913A1 (en) | 2001-08-30 | 2003-07-17 | 3M Innovative Properties Company | Methods of maturing plasmacytoid dendritic cells using immune response modifier molecules |
| EP1478371A4 (en) * | 2001-10-12 | 2007-11-07 | Univ Iowa Res Found | METHODS AND PRODUCTS FOR ENHANCING IMMUNE RESPONSES USING IMIDAZOQUINOLINE COMPOUND |
| DK1719511T3 (da) | 2001-11-16 | 2009-04-14 | Coley Pharm Group Inc | N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methansulfonamid, en farmaceutisk sammensætning omfattende samme, og anvendelse deraf |
| CA2467828C (en) | 2001-11-29 | 2011-10-04 | 3M Innovative Properties Company | Pharmaceutical formulations comprising an immune response modifier |
| CA2476626A1 (en) * | 2002-02-20 | 2003-08-28 | Chiron Corporation | Microparticles with adsorbed polypeptide-containing molecules |
| EP1478327B1 (en) | 2002-02-22 | 2015-04-29 | Meda AB | Method of reducing and treating uvb-induced immunosuppression |
| NZ535952A (en) | 2002-04-04 | 2009-01-31 | Coley Pharm Gmbh | Immunostimulatory G,U-containing oligoribonucleotides |
| AU2003225054A1 (en) | 2002-04-19 | 2003-11-03 | Yale University | Toll-like receptor 11 and toll-like receptor 12 |
| EP2939693A1 (en) * | 2003-08-14 | 2015-11-04 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
-
2003
- 2003-08-14 DK DK03808061.0T patent/DK1545597T3/da active
- 2003-08-14 EP EP03808061A patent/EP1545597B1/en not_active Expired - Lifetime
- 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 WO PCT/US2003/025523 patent/WO2004032829A2/en active Application Filing
- 2003-08-14 EP EP10181530.6A patent/EP2269632B1/en not_active Expired - Lifetime
- 2003-08-14 BR BRPI0313587-0A patent/BR0313587A/pt not_active IP Right Cessation
- 2003-08-14 US US10/640,904 patent/US7427629B2/en not_active Expired - Fee Related
- 2003-08-14 CA CA2495570A patent/CA2495570C/en not_active Expired - Fee Related
- 2003-08-14 DE DE60335010T patent/DE60335010D1/de not_active Expired - Lifetime
- 2003-08-14 PT PT03808061T patent/PT1545597E/pt unknown
- 2003-08-14 MX MXPA05001647A patent/MXPA05001647A/es active IP Right Grant
- 2003-08-14 NZ NZ538812A patent/NZ538812A/en not_active IP Right Cessation
- 2003-08-14 ES ES03808061T patent/ES2355819T3/es not_active Expired - Lifetime
- 2003-08-14 AT AT03808061T patent/ATE488246T1/de active
- 2003-08-14 JP JP2004543241A patent/JP4860923B2/ja not_active Expired - Fee Related
- 2003-08-14 KR KR1020057002485A patent/KR101088615B1/ko active IP Right Grant
-
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 |
| WO2002046189A2 (en) * | 2000-12-08 | 2002-06-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| WO2002046188A2 (en) * | 2000-12-08 | 2002-06-13 | 3M Innovative Properties Company | Amido 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 |
|---|---|
| WO2004032829A2 (en) | 2004-04-22 |
| US7427629B2 (en) | 2008-09-23 |
| PT1545597E (pt) | 2010-12-29 |
| MXPA05001647A (es) | 2005-04-19 |
| KR101088615B1 (ko) | 2011-11-30 |
| CA2495570A1 (en) | 2004-04-22 |
| EP2269632B1 (en) | 2014-01-01 |
| EP1545597A2 (en) | 2005-06-29 |
| US20040091491A1 (en) | 2004-05-13 |
| NZ538812A (en) | 2009-02-28 |
| CN1671412B (zh) | 2010-05-26 |
| ES2355819T3 (es) | 2011-03-31 |
| DK1545597T3 (da) | 2011-01-31 |
| WO2004032829A3 (en) | 2004-12-09 |
| DE60335010D1 (de) | 2010-12-30 |
| EP2269632A3 (en) | 2012-10-24 |
| JP2006507265A (ja) | 2006-03-02 |
| ATE488246T1 (de) | 2010-12-15 |
| JP4860923B2 (ja) | 2012-01-25 |
| JP2011057699A (ja) | 2011-03-24 |
| AU2003299863A2 (en) | 2004-05-04 |
| CN1671412A (zh) | 2005-09-21 |
| EP1545597A4 (en) | 2006-08-30 |
| CA2495570C (en) | 2012-12-04 |
| AU2003299863A1 (en) | 2004-05-04 |
| KR20050026709A (ko) | 2005-03-15 |
| JP5491364B2 (ja) | 2014-05-14 |
| EP1545597B1 (en) | 2010-11-17 |
| EP2269632A2 (en) | 2011-01-05 |
| BR0313587A (pt) | 2006-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2003299863B2 (en) | Immunostimulatory compositions and methods of stimulating an immune response | |
| JP6430574B2 (ja) | ヒドラジノ１ｈ−イミダゾキノリン−４−アミン及びこれから調製された複合体 | |
| US10472420B2 (en) | Immune response modifier conjugates | |
| US20060045885A1 (en) | Method of eliciting an immune response against HIV | |
| US20060045886A1 (en) | HIV immunostimulatory compositions | |
| AU2005244260B2 (en) | Methods, compositions, and preparations for delivery of immune response modifiers | |
| JP6460789B2 (ja) | ポリエチレングリコールセグメントを有するヘテロ２官能性リンカー及び該リンカーから調製された免疫反応調節複合体 | |
| JP2014532799A (ja) | 免疫調節結合体 | |
| AU2012261966B2 (en) | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
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 |