CA1225591A - Refined detoxified endotoxin product - Google Patents
Refined detoxified endotoxin productInfo
- Publication number
- CA1225591A CA1225591A CA000428677A CA428677A CA1225591A CA 1225591 A CA1225591 A CA 1225591A CA 000428677 A CA000428677 A CA 000428677A CA 428677 A CA428677 A CA 428677A CA 1225591 A CA1225591 A CA 1225591A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- methanol
- detoxified endotoxin
- chloroform
- micrograms
- 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.)
- Expired
Links
- 239000002158 endotoxin Substances 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 36
- XETCRXVKJHBPMK-MJSODCSWSA-N trehalose 6,6'-dimycolate Chemical compound C([C@@H]1[C@H]([C@H](O)[C@@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](COC(=O)C(CCCCCCCCCCC3C(C3)CCCCCCCCCCCCCCCCCC)C(O)CCCCCCCCCCCCCCCCCCCCCCCCC)O2)O)O1)O)OC(=O)C(C(O)CCCCCCCCCCCCCCCCCCCCCCCCC)CCCCCCCCCCC1CC1CCCCCCCCCCCCCCCCCC XETCRXVKJHBPMK-MJSODCSWSA-N 0.000 claims abstract description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 20
- 231100000284 endotoxic Toxicity 0.000 claims abstract description 8
- 230000002346 endotoxic effect Effects 0.000 claims abstract description 8
- 239000006227 byproduct Substances 0.000 claims abstract description 6
- 229930186217 Glycolipid Natural products 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 22
- 238000000034 method Methods 0.000 abstract description 10
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 241000700198 Cavia Species 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 230000004614 tumor growth Effects 0.000 description 7
- GZQKNULLWNGMCW-PWQABINMSA-N lipid A (E. coli) Chemical compound 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 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 241000282412 Homo Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000001373 regressive effect Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 241000282465 Canis Species 0.000 description 3
- 241000283073 Equus caballus Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000186367 Mycobacterium avium Species 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 201000001441 melanoma Diseases 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002510 pyrogen Substances 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- NSFMUHNGROVPRE-UHFFFAOYSA-N 7-hexyloctadecane Chemical compound CCCCCCCCCCCC(CCCCCC)CCCCCC NSFMUHNGROVPRE-UHFFFAOYSA-N 0.000 description 1
- 208000003200 Adenoma Diseases 0.000 description 1
- 206010001233 Adenoma benign Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000588807 Bordetella Species 0.000 description 1
- 241000588832 Bordetella pertussis Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 241000589562 Brucella Species 0.000 description 1
- 241000589567 Brucella abortus Species 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 108010039939 Cell Wall Skeleton Proteins 0.000 description 1
- 241000588923 Citrobacter Species 0.000 description 1
- 241000186216 Corynebacterium Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 241001467552 Mycobacterium bovis BCG Species 0.000 description 1
- 241000186363 Mycobacterium kansasii Species 0.000 description 1
- 241000187481 Mycobacterium phlei Species 0.000 description 1
- 241000588653 Neisseria Species 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 0.000 description 1
- 241000187563 Rhodococcus ruber Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000607662 Salmonella enterica subsp. enterica serovar Abortusequi Species 0.000 description 1
- 241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 1
- 241001222774 Salmonella enterica subsp. enterica serovar Minnesota Species 0.000 description 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000031844 Squamous cell carcinoma of the rectum Diseases 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 210000004520 cell wall skeleton Anatomy 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007689 endotoxicity Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940059904 light mineral oil Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 208000037841 lung tumor Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 208000013718 rectal benign neoplasm Diseases 0.000 description 1
- 201000001276 rectum malignant melanoma Diseases 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 208000012977 squamous cell carcinoma of rectum Diseases 0.000 description 1
- 230000035322 succinylation Effects 0.000 description 1
- 238000010613 succinylation reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/66—Microorganisms or materials therefrom
- A61K35/74—Bacteria
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7016—Disaccharides, e.g. lactose, lactulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
-
- 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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US382,406 | 1982-05-26 | ||
| US06/382,406 US4435386A (en) | 1982-05-26 | 1982-05-26 | Refined detoxified endotoxin product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1225591A true CA1225591A (en) | 1987-08-18 |
Family
ID=23508812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000428677A Expired CA1225591A (en) | 1982-05-26 | 1983-05-24 | Refined detoxified endotoxin product |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4435386A (en, 2012) |
| JP (1) | JPS58222027A (en, 2012) |
| CA (1) | CA1225591A (en, 2012) |
| DE (1) | DE3318568C2 (en, 2012) |
| FR (1) | FR2527444B1 (en, 2012) |
| GB (1) | GB2122084B (en, 2012) |
| IT (1) | IT1164244B (en, 2012) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4505899A (en) * | 1982-05-26 | 1985-03-19 | Ribi Immunochem Research, Inc. | Refined detoxified endotoxin product |
| US4866034A (en) * | 1982-05-26 | 1989-09-12 | Ribi Immunochem Research Inc. | Refined detoxified endotoxin |
| CA1225592A (en) * | 1983-08-26 | 1987-08-18 | Ribi Immunochem Research Inc. | Refined detoxified endotoxin |
| US4663306A (en) * | 1983-09-23 | 1987-05-05 | Ribi Immunochem Research, Inc. | Pyridine-soluble extract-refined detoxified endotoxin composition and use |
| US4497730A (en) * | 1984-04-03 | 1985-02-05 | The United States Of America As Represented By The Department Of Health And Human Services | Method for obtaining periplasmic proteins from bacterial cells using chloroform |
| NL8401226A (nl) * | 1984-04-16 | 1985-11-18 | Univ Utrecht | Farmaceutisch produkt met anti-tumorwerking; gebruik van een farmaceutisch produkt of van farmaceutische samenstellingen in een anti-tumortherapie. |
| US4629722A (en) * | 1984-07-12 | 1986-12-16 | Ribi Immunochem Research, Inc. | Method of inhibiting the onset of acute radiation syndrome |
| US4929604A (en) * | 1986-05-28 | 1990-05-29 | Board Of Regents, The University Of Texas System | Lipopolysaccharides of reduced toxicity and the production thereof |
| US4845036A (en) * | 1987-02-03 | 1989-07-04 | The United States Of America As Represented By The Department Of Health And Human Services | Process for isolation of the B oligomer of pertussis toxin |
| US5416070A (en) * | 1988-07-08 | 1995-05-16 | Immunotherapeutics, Inc. | Composition for macrophage activation |
| US4950645A (en) * | 1988-07-08 | 1990-08-21 | Immunotherapeutics, Inc. | Composition for macrophage activation |
| US6218166B1 (en) | 1994-12-09 | 2001-04-17 | John Wayne Cancer Institute | Adjuvant incorporation into antigen carrying cells: compositions and methods |
| WO1998035665A1 (fr) * | 1997-02-14 | 1998-08-20 | Ajinomoto Co., Inc. | Antagonistes des endotoxines |
| AU4057300A (en) * | 1999-03-30 | 2000-10-16 | Board Of Regents, The University Of Texas System | Compositions and methods for modifying toxic effects of proteinacious compounds |
| US20040002068A1 (en) | 2000-03-01 | 2004-01-01 | Corixa Corporation | Compositions and methods for the detection, diagnosis and therapy of hematological malignancies |
| US20030224013A1 (en) * | 2002-04-19 | 2003-12-04 | Cole Garry T. | Methods for protection against Coccidioides spp. infection using Coccidioides spp. urea amidohydrolase (Ure) protein |
| US20040175378A1 (en) | 2002-07-15 | 2004-09-09 | Board Of Regents, The University Of Texas System | Selected antibody compositions and methods for binding to aminophospholipids |
| US8128921B2 (en) * | 2006-07-11 | 2012-03-06 | University Of Connecticut | Use of conditional plasmodium strains lacking nutrient transporters in malaria vaccination |
| US20120244185A1 (en) | 2009-09-16 | 2012-09-27 | Vaxart ,Inc. | Immunization strategy to prevent h1n1 infection |
| EP3711768A1 (en) | 2013-04-18 | 2020-09-23 | Immune Design Corp. | Gla monotherapy for use in cancer treatment |
| US9463198B2 (en) | 2013-06-04 | 2016-10-11 | Infectious Disease Research Institute | Compositions and methods for reducing or preventing metastasis |
| US10751410B2 (en) | 2013-09-19 | 2020-08-25 | Novavax, Inc. | Immunogenic middle east respiratory syndrome coronavirus (MERS-CoV) compositions and methods |
| US20170224805A1 (en) | 2014-02-20 | 2017-08-10 | Vaxart, Inc. | Formulations for small intestinal delivery |
| CN118045170A (zh) | 2015-06-12 | 2024-05-17 | 瓦克萨特公司 | 用于rsv和诺如病毒抗原的小肠递送的制剂 |
| EP3423044A4 (en) | 2016-03-02 | 2019-11-20 | The Board of Regents of The University of Texas System | STING-ACTIVATING NANO VACCINE FOR IMMUNOTHERAPY |
| US11850279B2 (en) | 2016-07-13 | 2023-12-26 | Ohio State Innovation Foundation | Platforms and methods for optimizing host antigen presentation and host antitumor and antipathogen immunity |
| US11376320B2 (en) | 2020-03-05 | 2022-07-05 | Iowa State University Research Foundation, Inc. | Immunogenic and vaccine compositions against SARS-CoV-2 |
-
1982
- 1982-05-26 US US06/382,406 patent/US4435386A/en not_active Expired - Lifetime
-
1983
- 1983-05-12 GB GB08313054A patent/GB2122084B/en not_active Expired
- 1983-05-20 DE DE3318568A patent/DE3318568C2/de not_active Expired
- 1983-05-24 CA CA000428677A patent/CA1225591A/en not_active Expired
- 1983-05-25 FR FR8308586A patent/FR2527444B1/fr not_active Expired
- 1983-05-25 JP JP58090858A patent/JPS58222027A/ja active Granted
- 1983-05-25 IT IT21289/83A patent/IT1164244B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2527444B1 (fr) | 1987-02-20 |
| IT1164244B (it) | 1987-04-08 |
| JPS6234730B2 (en, 2012) | 1987-07-28 |
| DE3318568C2 (de) | 1987-01-15 |
| GB2122084A (en) | 1984-01-11 |
| GB8313054D0 (en) | 1983-06-15 |
| FR2527444A1 (fr) | 1983-12-02 |
| US4435386A (en) | 1984-03-06 |
| GB2122084B (en) | 1986-02-05 |
| JPS58222027A (ja) | 1983-12-23 |
| DE3318568A1 (de) | 1984-01-12 |
| IT8321289A0 (it) | 1983-05-25 |
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