AU775942B2 - Aqueous immunologic adjuvant compositions of monophosphoryl lipid A - Google Patents
Aqueous immunologic adjuvant compositions of monophosphoryl lipid A Download PDFInfo
- Publication number
- AU775942B2 AU775942B2 AU58738/00A AU5873800A AU775942B2 AU 775942 B2 AU775942 B2 AU 775942B2 AU 58738/00 A AU58738/00 A AU 58738/00A AU 5873800 A AU5873800 A AU 5873800A AU 775942 B2 AU775942 B2 AU 775942B2
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- AU
- Australia
- Prior art keywords
- mla
- lipid
- surfactant
- antigen
- aqueous
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 229940035032 monophosphoryl lipid a Drugs 0.000 title claims abstract description 66
- 239000000568 immunological adjuvant Substances 0.000 title description 3
- 239000004094 surface-active agent Substances 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000009472 formulation Methods 0.000 claims abstract description 20
- 239000002671 adjuvant Substances 0.000 claims abstract description 13
- 230000003308 immunostimulating effect Effects 0.000 claims abstract description 12
- 239000000725 suspension Substances 0.000 claims abstract description 12
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims abstract description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- 239000002245 particle Substances 0.000 claims description 12
- -1 poly(propylene glycol) Polymers 0.000 claims description 5
- 238000000527 sonication Methods 0.000 claims description 5
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 102000036639 antigens Human genes 0.000 abstract description 35
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- 239000000427 antigen Substances 0.000 abstract description 32
- GZQKNULLWNGMCW-PWQABINMSA-N lipid A (E. coli) Chemical class O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OP(O)(O)=O)O1 GZQKNULLWNGMCW-PWQABINMSA-N 0.000 abstract description 28
- 230000002238 attenuated effect Effects 0.000 abstract description 17
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- 239000002904 solvent Substances 0.000 abstract description 13
- 210000002966 serum Anatomy 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 230000004044 response Effects 0.000 abstract description 8
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- 230000002062 proliferating effect Effects 0.000 abstract 1
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- 230000003053 immunization Effects 0.000 description 20
- 238000002649 immunization Methods 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 17
- 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 17
- 239000002953 phosphate buffered saline Substances 0.000 description 17
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- 229960005486 vaccine Drugs 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002158 endotoxin Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229920006008 lipopolysaccharide Polymers 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- 108010058846 Ovalbumin Proteins 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 150000004665 fatty acids Chemical group 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
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- 229940092253 ovalbumin Drugs 0.000 description 5
- 239000008215 water for injection Substances 0.000 description 5
- 238000002965 ELISA Methods 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 230000024932 T cell mediated immunity Effects 0.000 description 4
- 239000012636 effector Substances 0.000 description 4
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- 238000011160 research Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 210000001744 T-lymphocyte Anatomy 0.000 description 3
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- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 3
- 238000002784 cytotoxicity assay Methods 0.000 description 3
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- 229960002442 glucosamine Drugs 0.000 description 3
- 208000002672 hepatitis B Diseases 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
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- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 210000002925 A-like Anatomy 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101710154606 Hemagglutinin Proteins 0.000 description 2
- 101710093908 Outer capsid protein VP4 Proteins 0.000 description 2
- 101710135467 Outer capsid protein sigma-1 Proteins 0.000 description 2
- 101710176177 Protein A56 Proteins 0.000 description 2
- 241001222774 Salmonella enterica subsp. enterica serovar Minnesota Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012062 aqueous buffer Substances 0.000 description 2
- 239000003833 bile salt Substances 0.000 description 2
- 229940093761 bile salts Drugs 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
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- 238000005947 deacylation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000185 hemagglutinin Substances 0.000 description 2
- 229960001438 immunostimulant agent Drugs 0.000 description 2
- 239000003022 immunostimulating agent Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
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- 206010022000 influenza Diseases 0.000 description 2
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- 150000007529 inorganic bases Chemical class 0.000 description 2
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- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002510 pyrogen Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 150000003408 sphingolipids Chemical class 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
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- 238000002255 vaccination Methods 0.000 description 2
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 description 1
- NEZDNQCXEZDCBI-WJOKGBTCSA-N (2-aminoethoxy)[(2r)-2,3-bis(tetradecanoyloxy)propoxy]phosphinic acid Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC NEZDNQCXEZDCBI-WJOKGBTCSA-N 0.000 description 1
- IQFYYKKMVGJFEH-OFKYTIFKSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(tritiooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](CO[3H])O[C@H]1N1C(=O)NC(=O)C(C)=C1 IQFYYKKMVGJFEH-OFKYTIFKSA-N 0.000 description 1
- 238000011725 BALB/c mouse Methods 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000305071 Enterobacterales Species 0.000 description 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
- 108010035713 Glycodeoxycholic Acid Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 231100000111 LD50 Toxicity 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000037581 Persistent Infection Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000008349 antigen-specific humoral response Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000001516 cell proliferation assay Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 210000003837 chick embryo Anatomy 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
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- 230000009089 cytolysis Effects 0.000 description 1
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- 229940009976 deoxycholate Drugs 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
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- WVULKSPCQVQLCU-BUXLTGKBSA-N glycodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 WVULKSPCQVQLCU-BUXLTGKBSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
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- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
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- 208000037797 influenza A Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000021633 leukocyte mediated immunity Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 230000016379 mucosal immune response Effects 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- VOXDTCSXQHOYKC-XGEOUJBZSA-N palmitoyllipid A Chemical compound O[C@H]1[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)[C@@H](OP(O)(O)=O)O[C@@H]1CO[C@H]1[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@H](OP(O)(O)=O)[C@@H](CO)O1 VOXDTCSXQHOYKC-XGEOUJBZSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 235000017550 sodium carbonate Nutrition 0.000 description 1
- PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
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- 239000006228 supernatant Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229940021747 therapeutic vaccine Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0043—Nose
-
- 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
- A61K2039/55555—Liposomes; Vesicles, e.g. nanoparticles; Spheres, e.g. nanospheres; Polymers
-
- 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
- A61K2039/55572—Lipopolysaccharides; Lipid A; Monophosphoryl lipid A
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Otolaryngology (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/338,182 US6491919B2 (en) | 1997-04-01 | 1999-06-22 | Aqueous immunologic adjuvant compostions of monophosphoryl lipid A |
| US09/338182 | 1999-06-22 | ||
| PCT/US2000/016384 WO2000078353A2 (en) | 1999-06-22 | 2000-06-14 | Aqueous immunologic adjuvant compositions of monophosphoryl lipid a |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5873800A AU5873800A (en) | 2001-01-09 |
| AU775942B2 true AU775942B2 (en) | 2004-08-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU58738/00A Ceased AU775942B2 (en) | 1999-06-22 | 2000-06-14 | Aqueous immunologic adjuvant compositions of monophosphoryl lipid A |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6491919B2 (enExample) |
| EP (1) | EP1194166B1 (enExample) |
| JP (1) | JP2003502388A (enExample) |
| AT (1) | ATE381344T1 (enExample) |
| AU (1) | AU775942B2 (enExample) |
| CA (1) | CA2376829A1 (enExample) |
| DE (1) | DE60037514T2 (enExample) |
| ES (1) | ES2296629T3 (enExample) |
| WO (1) | WO2000078353A2 (enExample) |
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| GB0000891D0 (en) * | 2000-01-14 | 2000-03-08 | Allergy Therapeutics Ltd | Formulation |
| BR0110975A (pt) * | 2000-05-19 | 2004-03-23 | Corixa Corp | Tratamento profilático e terapêutico de doenças infecciosas ou outras doenças com compostos à base de mono- e disacarìdeos |
| US20030139356A1 (en) * | 2001-05-18 | 2003-07-24 | Persing David H. | Prophylactic and therapeutic treatment of infectious and other diseases with mono- and disaccharide-based compounds |
| US20030031684A1 (en) * | 2001-03-30 | 2003-02-13 | Corixa Corporation | Methods for the production of 3-O-deactivated-4'-monophosphoryl lipid a (3D-MLA) |
| JP2009509970A (ja) * | 2005-09-22 | 2009-03-12 | プロサイ インコーポレイテッド | 酵母突然変異体において産生されるグリコシル化ポリペプチドおよびその使用方法 |
| US7622128B2 (en) * | 2005-12-13 | 2009-11-24 | University Of Washington | Porphyromonas gingivalis 1435/1449 LPS as an immune modulator |
| WO2007079193A2 (en) | 2005-12-30 | 2007-07-12 | Tti Ellebeau, Inc. | Iontophoretic systems, devices, and methods of delivery of active agents to biological interface |
| WO2008153541A1 (en) | 2006-09-26 | 2008-12-18 | Infectious Disease Research Institute | Vaccine composition containing synthetic adjuvant |
| US20090181078A1 (en) | 2006-09-26 | 2009-07-16 | Infectious Disease Research Institute | Vaccine composition containing synthetic adjuvant |
| AU2007303608B2 (en) | 2006-09-29 | 2013-05-02 | Takeda Vaccines, Inc. | Norovirus vaccine formulations |
| CN101918028B (zh) | 2007-09-18 | 2015-01-07 | 莱戈赛特医药股份有限公司 | 赋予针对诺如病毒的保护性免疫应答的疫苗 |
| US20100266636A1 (en) * | 2007-09-18 | 2010-10-21 | Ligocyte Pharmaceuticals, Inc. | Method of conferring a protective immune response to norovirus |
| US9415006B2 (en) * | 2008-05-23 | 2016-08-16 | The Regents Of The University Of Michigan | Immunogenic compositions comprising nanoemulsion and hepatitis B virus immunogen and methods of using the same |
| JP5852883B2 (ja) * | 2008-08-08 | 2016-02-03 | タケダ ワクチン，インコーポレイテッド | 交差反応性の増強のための複合カプシドアミノ酸配列を含むウイルス様粒子 |
| CN102223876A (zh) | 2008-09-26 | 2011-10-19 | 纳米生物公司 | 纳米乳剂治疗性组合物及其使用方法 |
| EP3124491B1 (en) | 2009-06-05 | 2019-10-30 | Infectious Disease Research Institute | Synthetic glucopyranosyl lipid adjuvants and vaccine compositions as well as pharmaceutical compositions containing them |
| ES2566646T3 (es) * | 2009-06-16 | 2016-04-14 | The Regents Of The University Of Michigan | Vacunas en nanoemulsión |
| AU2012243039B2 (en) | 2011-04-08 | 2017-07-13 | Immune Design Corp. | Immunogenic compositions and methods of using the compositions for inducing humoral and cellular immune responses |
| DK3299030T3 (da) | 2011-07-11 | 2022-09-05 | Takeda Vaccines Inc | Parenterale norovirus-vaccineformuleringer |
| US20150190501A1 (en) | 2011-09-12 | 2015-07-09 | Imperial Innovations Limited | Methods and compositions for raising an immune response to hiv |
| EA034351B1 (ru) | 2012-05-16 | 2020-01-30 | Иммьюн Дизайн Корп. | Трехкомпонентная вакцина против впг-2 и способы ее применения |
| CN105209047B (zh) | 2013-04-18 | 2020-08-18 | 免疫设计股份有限公司 | 用于癌症治疗的gla单一疗法 |
| US9463198B2 (en) | 2013-06-04 | 2016-10-11 | Infectious Disease Research Institute | Compositions and methods for reducing or preventing metastasis |
| US9017698B2 (en) | 2013-09-25 | 2015-04-28 | Sequoia Sciences, Inc. | Compositions of vaccines and adjuvants and methods for the treatment of urinary tract infections |
| US10420833B2 (en) | 2014-05-19 | 2019-09-24 | Board Of Regents, The University Of Texas System | Combinatorial platform for the display of surface adjuvants and antigens |
| EP3069729A1 (en) | 2015-03-17 | 2016-09-21 | Sequoia Sciences, Inc. | Compositions of vaccines and adjuvants and methods for the treatment of urinary tract infections |
| WO2019175145A1 (en) | 2018-03-12 | 2019-09-19 | Janssen Vaccines & Prevention B.V. | Vaccines against urinary tract infections |
| US11446370B2 (en) | 2019-03-18 | 2022-09-20 | Janssen Pharmaceuticals, Inc. | Bioconjugates of E. coli o-antigen polysaccharides, methods of production thereof, and methods of use thereof |
| IL286467B1 (en) | 2019-03-18 | 2025-10-01 | Janssen Pharmaceuticals Inc | Methods for producing bioconjugates of E. COLI O-antigen polysaccharides, preparations thereof and methods for using them |
| WO2021067785A1 (en) | 2019-10-02 | 2021-04-08 | Janssen Vaccines & Prevention B.V | Staphylococcus peptides and methods of use |
| IL294445B2 (en) | 2020-01-16 | 2023-10-01 | Janssen Pharmaceuticals Inc | FIMH mutant, its preparations and their use |
| BR112023004819A2 (pt) | 2020-09-17 | 2023-04-18 | Janssen Pharmaceuticals Inc | Composições de vacinas multivalentes e seus usos |
| KR20250007029A (ko) | 2021-01-12 | 2025-01-13 | 얀센 파마슈티칼즈, 인코포레이티드 | FimH 돌연변이체, 이를 포함하는 조성물 및 이의 용도 |
| UY39710A (es) | 2021-04-01 | 2022-09-30 | Janssen Pharmaceuticals Inc | Producción de bioconjugados de o18 de e. coli |
| WO2022251455A1 (en) * | 2021-05-27 | 2022-12-01 | Revelation Biosciences, Inc. | Methods of treating or preventing allergies and chronic nasal congestion |
| WO2025058011A1 (ja) * | 2023-09-13 | 2025-03-20 | 国立大学法人大阪大学 | 経鼻投与用組成物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5552141A (en) * | 1991-10-30 | 1996-09-03 | Ribi; Hans O. | Polymeric immunological adjuvants |
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| US4436727A (en) * | 1982-05-26 | 1984-03-13 | Ribi Immunochem Research, Inc. | Refined detoxified endotoxin product |
| US4436728A (en) * | 1982-05-26 | 1984-03-13 | Ribi Immunochem Research, Inc. | Refined detoxified endotoxin product |
| US5554372A (en) * | 1986-09-22 | 1996-09-10 | Emory University | Methods and vaccines comprising surface-active copolymers |
| US4912094B1 (en) * | 1988-06-29 | 1994-02-15 | Ribi Immunochem Research Inc. | Modified lipopolysaccharides and process of preparation |
| US5068191A (en) * | 1989-08-31 | 1991-11-26 | The Biomembrane Institute | Purified histo-blood group a glycosyltransferase and antibodies thereto |
| FR2672496B3 (fr) * | 1990-07-18 | 1993-05-28 | Vacsyn France Sa | Compositions a base de substances hydrophobes, solubilisables dans un solvant aqueux, leur procede d'obtention, et leurs utilisations notamment dans le domaine pharmaceutique. |
| US7014856B1 (en) * | 1993-01-22 | 2006-03-21 | Sloan-Kettering Institute For Cancer Research | Ganglioside-KLH conjugate vaccines plus OS-21 |
| DK0689454T4 (da) | 1993-03-23 | 2005-05-30 | Smithkline Beecham Biolog | Vaccinepræparater indeholdende 3-O-deacyleret monophosphoryl-lipid A |
| US5985309A (en) * | 1996-05-24 | 1999-11-16 | Massachusetts Institute Of Technology | Preparation of particles for inhalation |
| US5855913A (en) | 1997-01-16 | 1999-01-05 | Massachusetts Instite Of Technology | Particles incorporating surfactants for pulmonary drug delivery |
| CN1259052A (zh) | 1997-04-01 | 2000-07-05 | 科里克萨有限公司 | 单磷酰基脂质a的水性免疫佐剂组合物 |
| CA2330610A1 (en) | 1998-05-07 | 1999-11-11 | Corixa Corporation | Adjuvant composition and methods for its use |
-
1999
- 1999-06-22 US US09/338,182 patent/US6491919B2/en not_active Expired - Lifetime
-
2000
- 2000-06-14 CA CA002376829A patent/CA2376829A1/en not_active Abandoned
- 2000-06-14 AT AT00944677T patent/ATE381344T1/de not_active IP Right Cessation
- 2000-06-14 DE DE60037514T patent/DE60037514T2/de not_active Expired - Fee Related
- 2000-06-14 AU AU58738/00A patent/AU775942B2/en not_active Ceased
- 2000-06-14 WO PCT/US2000/016384 patent/WO2000078353A2/en not_active Ceased
- 2000-06-14 JP JP2001504415A patent/JP2003502388A/ja active Pending
- 2000-06-14 EP EP00944677A patent/EP1194166B1/en not_active Expired - Lifetime
- 2000-06-14 ES ES00944677T patent/ES2296629T3/es not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5552141A (en) * | 1991-10-30 | 1996-09-03 | Ribi; Hans O. | Polymeric immunological adjuvants |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1194166A2 (en) | 2002-04-10 |
| EP1194166B1 (en) | 2007-12-19 |
| DE60037514D1 (de) | 2008-01-31 |
| DE60037514T2 (de) | 2008-12-24 |
| AU5873800A (en) | 2001-01-09 |
| ES2296629T3 (es) | 2008-05-01 |
| CA2376829A1 (en) | 2000-12-28 |
| US20020009456A1 (en) | 2002-01-24 |
| ATE381344T1 (de) | 2008-01-15 |
| US6491919B2 (en) | 2002-12-10 |
| WO2000078353A2 (en) | 2000-12-28 |
| WO2000078353A3 (en) | 2001-03-15 |
| JP2003502388A (ja) | 2003-01-21 |
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