NL8802595A - Derivaten van monofosforyl-lipide a en werkwijze voor de bereiding daarvan. - Google Patents
Derivaten van monofosforyl-lipide a en werkwijze voor de bereiding daarvan. Download PDFInfo
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- NL8802595A NL8802595A NL8802595A NL8802595A NL8802595A NL 8802595 A NL8802595 A NL 8802595A NL 8802595 A NL8802595 A NL 8802595A NL 8802595 A NL8802595 A NL 8802595A NL 8802595 A NL8802595 A NL 8802595A
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- lipid
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- 238000000034 method Methods 0.000 title claims description 36
- 238000002360 preparation method Methods 0.000 title claims description 13
- 229940035032 monophosphoryl lipid a Drugs 0.000 claims description 96
- -1 3- (2-pyridyldithio) propionyl) group Chemical group 0.000 claims description 22
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- 239000008280 blood Substances 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004520 cell wall skeleton Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- ZWIBGKZDAWNIFC-UHFFFAOYSA-N disuccinimidyl suberate Chemical compound O=C1CCC(=O)N1OC(=O)CCCCCCC(=O)ON1C(=O)CCC1=O ZWIBGKZDAWNIFC-UHFFFAOYSA-N 0.000 description 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N glucosamine group Chemical group OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960002743 glutamine Drugs 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 239000000367 immunologic factor Substances 0.000 description 1
- 238000010324 immunological assay Methods 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 230000002434 immunopotentiative effect Effects 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000015788 innate immune response Effects 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 229940124280 l-arginine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 230000015286 negative regulation of phagocytosis Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- NFBAXHOPROOJAW-UHFFFAOYSA-N phenindione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 NFBAXHOPROOJAW-UHFFFAOYSA-N 0.000 description 1
- 229960000280 phenindione Drugs 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000015323 positive regulation of phagocytosis Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/05—Immunological preparations stimulating the reticulo-endothelial system, e.g. against cancer
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K17/00—Carrier-bound or immobilised peptides; Preparation thereof
- C07K17/02—Peptides being immobilised on, or in, an organic carrier
- C07K17/06—Peptides being immobilised on, or in, an organic carrier attached to the carrier via a bridging agent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Immunology (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Microbiology (AREA)
- Mycology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11274287 | 1987-10-22 | ||
| US07/112,742 US4987237A (en) | 1983-08-26 | 1987-10-22 | Derivatives of monophosphoryl lipid A |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8802595A true NL8802595A (nl) | 1989-05-16 |
Family
ID=22345625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8802595A NL8802595A (nl) | 1987-10-22 | 1988-10-21 | Derivaten van monofosforyl-lipide a en werkwijze voor de bereiding daarvan. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4987237A (enExample) |
| JP (1) | JPH075623B2 (enExample) |
| BE (1) | BE1003250A5 (enExample) |
| CA (1) | CA1308711C (enExample) |
| CH (1) | CH676715A5 (enExample) |
| DE (1) | DE3836006C2 (enExample) |
| FR (1) | FR2622192A1 (enExample) |
| GB (1) | GB2211502B (enExample) |
| IT (1) | IT1230592B (enExample) |
| NL (1) | NL8802595A (enExample) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5158939A (en) * | 1989-07-21 | 1992-10-27 | Wisconsin Alumni Research Foundation | Method of stimulating the immune systems of animals and compositions useful therefor |
| US5334379A (en) * | 1989-07-14 | 1994-08-02 | American Cyanamid Company | Cytokine and hormone carriers for conjugate vaccines |
| US5498708A (en) * | 1989-07-18 | 1996-03-12 | Montefiore Medical Center | Method of synthesizing polyesters |
| KR940004071B1 (ko) * | 1990-04-12 | 1994-05-11 | 니홍 다바꼬 상교 가부시끼가이샤 | 4,6-o-히드록시포스포릴글루코사민 유도체 |
| US5653974A (en) * | 1990-10-18 | 1997-08-05 | Board Of Regents,The University Of Texas System | Preparation and characterization of liposomal formulations of tumor necrosis factor |
| US5164375A (en) * | 1991-09-27 | 1992-11-17 | Merck & Company, Inc. | Antifungal agent |
| US5648343A (en) * | 1994-02-28 | 1997-07-15 | The University Of Georgia Research Foundation | Method for treating LPS-mediated disorders |
| US6218166B1 (en) | 1994-12-09 | 2001-04-17 | John Wayne Cancer Institute | Adjuvant incorporation into antigen carrying cells: compositions and methods |
| US5750664A (en) * | 1995-06-05 | 1998-05-12 | Eisai Co., Ltd. | Substituted liposaccharides useful in the treatment and prevention of endotoxemia |
| US6290971B1 (en) * | 1995-06-15 | 2001-09-18 | Aventis Pasteur Limited | Adjuvant compositions comprising a mineral salt and another immunostimulating compound |
| GB9706957D0 (en) * | 1997-04-05 | 1997-05-21 | Smithkline Beecham Plc | Formulation |
| GB9820525D0 (en) | 1998-09-21 | 1998-11-11 | Allergy Therapeutics Ltd | Formulation |
| GB0000891D0 (en) | 2000-01-14 | 2000-03-08 | Allergy Therapeutics Ltd | Formulation |
| US20040002068A1 (en) | 2000-03-01 | 2004-01-01 | Corixa Corporation | Compositions and methods for the detection, diagnosis and therapy of hematological malignancies |
| 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 |
| US20030138769A1 (en) * | 2000-08-16 | 2003-07-24 | Birkett Ashley J. | Immunogenic HBc chimer particles having enhanced stability |
| US20030185858A1 (en) * | 2001-08-15 | 2003-10-02 | Birkett Ashley J. | Immunogenic HBc chimer particles stabilized with an N-terminal cysteine |
| US7361352B2 (en) * | 2001-08-15 | 2008-04-22 | Acambis, Inc. | Influenza immunogen and vaccine |
| US20030175863A1 (en) * | 2001-08-15 | 2003-09-18 | Birkett Ashley J. | Influenza immunogen and vaccine |
| US6911434B2 (en) * | 2002-02-04 | 2005-06-28 | Corixa Corporation | Prophylactic and therapeutic treatment of infectious and other diseases with immunoeffector compounds |
| PT1482795E (pt) * | 2002-02-04 | 2010-02-09 | Corixa Corp | Novos compostos efectores imunológicos |
| WO2003073827A2 (en) * | 2002-02-28 | 2003-09-12 | Corixa Corporation | Methods of modulating dendritic cells using adjuvants |
| 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 |
| NZ537655A (en) | 2002-07-08 | 2006-12-22 | Corixa Corp | Processes for the production of aminoalkyl glucosaminide phosphate and disaccharide immunoeffectors, and intermediates therefor |
| MXPA05007295A (es) | 2003-01-06 | 2005-09-30 | Corixa Corp | Ciertos compuestos de fosfato de aminoalquil glucosaminida y su uso. |
| US7960522B2 (en) | 2003-01-06 | 2011-06-14 | Corixa Corporation | Certain aminoalkyl glucosaminide phosphate compounds and their use |
| ATE324903T1 (de) * | 2003-02-18 | 2006-06-15 | Clinique La Prairie Res Sa | Zusammensetzungen enthaltend fötales hämoglobin und bakterielles endotoxin und fakultativ zusätzliche fötale leberkomponenten |
| EP1835935A4 (en) * | 2004-12-30 | 2009-06-17 | Univ Rockefeller | COMPOSITIONS AND METHODS FOR ENHANCING THE MATURATION AND FUNCTION OF DENDRITIC CELLS |
| US20060210590A1 (en) | 2005-02-03 | 2006-09-21 | Alk-Abello A/S | Minor allergen control to increase safety of immunotherapy |
| US7622128B2 (en) * | 2005-12-13 | 2009-11-24 | University Of Washington | Porphyromonas gingivalis 1435/1449 LPS as an immune modulator |
| US20090181078A1 (en) | 2006-09-26 | 2009-07-16 | Infectious Disease Research Institute | Vaccine composition containing synthetic adjuvant |
| LT2484375T (lt) | 2006-09-26 | 2018-07-10 | Infectious Disease Research Institute | Vakcinos kompozicija, turinti sintetinio adjuvanto |
| JP5654345B2 (ja) | 2007-08-02 | 2015-01-14 | ビオンドヴァックス ファーマシューティカルズ リミテッド | 多量体マルチエピトープインフルエンザワクチン |
| US20090215710A1 (en) * | 2007-09-24 | 2009-08-27 | Reliance Life Sciences Pvt. Ltd. | Carbohydrate based toll-like receptor (tlr) antagonists |
| US20090215908A1 (en) * | 2007-09-24 | 2009-08-27 | Reliance Life Sciences Pvt. Ltd. | Toll like receptor (tlr) signaling antagonist |
| WO2009073179A2 (en) | 2007-12-03 | 2009-06-11 | President And Fellows Of Harvard College | Chlamydia antigens |
| LT2437753T (lt) * | 2009-06-05 | 2016-12-12 | Infectious Disease Research Institute | Sintetiniai gliukopiranozillipidų adjuvantai ir juos turinčios vakcinų kompozicijos |
| WO2012114323A1 (en) | 2011-02-22 | 2012-08-30 | Biondvax Pharmaceuticals Ltd. | Multimeric multiepitope polypeptides in improved seasonal and pandemic influenza vaccines |
| WO2012141984A1 (en) | 2011-04-08 | 2012-10-18 | Immune Design Corp. | Immunogenic compositions and methods of using the compositions for inducing humoral and cellular immune responses |
| GB201106802D0 (en) | 2011-04-21 | 2011-06-01 | Allergy Therapeutics Ltd | Process for preparing vaccine composition |
| EA034351B1 (ru) | 2012-05-16 | 2020-01-30 | Иммьюн Дизайн Корп. | Трехкомпонентная вакцина против впг-2 и способы ее применения |
| EP2953638B1 (en) | 2013-02-07 | 2023-07-05 | Children's Medical Center Corporation | Protein antigens that provide protection against pneumococcal colonization and/or disease |
| CN105658661B (zh) | 2013-02-20 | 2020-07-24 | 卑尔根技术交易股份公司 | 疫苗 |
| HK1214510A1 (zh) | 2013-04-18 | 2016-07-29 | Immune Design Corp. | 用於癌症治疗的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 |
| ES3020582T3 (en) | 2013-07-26 | 2025-05-23 | Inst Nat Sante Rech Med | Methods and pharmaceutical compositions for the treatment of bacterial infections |
| WO2016180852A1 (en) | 2015-05-12 | 2016-11-17 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for preparing antigen-specific t cells from an umbilical cord blood sample |
| EP3681534A1 (en) | 2017-09-13 | 2020-07-22 | Sanofi Pasteur | Human cytomegalovirus immunogenic composition |
| WO2019175145A1 (en) | 2018-03-12 | 2019-09-19 | Janssen Vaccines & Prevention B.V. | Vaccines against urinary tract infections |
| US20220249644A1 (en) | 2018-08-24 | 2022-08-11 | Vestlandets Innovasjonsselskap As (Vis) | Heat-Stable Enterotoxins Mutants as Antidiarrheal Vaccine Antigens |
| EP4038091A1 (en) | 2019-10-02 | 2022-08-10 | Janssen Vaccines & Prevention B.V. | Staphylococcus peptides and methods of use |
| KR20220128372A (ko) | 2020-01-16 | 2022-09-20 | 얀센 파마슈티칼즈, 인코포레이티드 | Fimh 돌연변이체, 이를 갖는 조성물 및 이의 용도 |
| KR102746713B1 (ko) | 2021-01-12 | 2024-12-24 | 얀센 파마슈티칼즈, 인코포레이티드 | FimH 돌연변이체, 이를 포함하는 조성물 및 이의 용도 |
| CN117222427A (zh) | 2021-04-01 | 2023-12-12 | 杨森制药公司 | 大肠杆菌o18生物缀合物的生产 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0414725Y2 (enExample) * | 1980-09-30 | 1992-04-02 | ||
| 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 |
| JPS62129293A (ja) * | 1985-11-28 | 1987-06-11 | Toho Yakuhin Kogyo Kk | 親水性のリピドａ単糖類縁体 |
| JPS62195396A (ja) * | 1986-02-20 | 1987-08-28 | Toho Yakuhin Kogyo Kk | 親水性及び疎水性の基を置換したりピドａ単糖類縁体 |
-
1987
- 1987-10-22 US US07/112,742 patent/US4987237A/en not_active Expired - Lifetime
-
1988
- 1988-10-14 CA CA000580545A patent/CA1308711C/en not_active Expired - Lifetime
- 1988-10-18 GB GB8824330A patent/GB2211502B/en not_active Expired - Lifetime
- 1988-10-20 BE BE8801207A patent/BE1003250A5/fr not_active IP Right Cessation
- 1988-10-21 FR FR8813812A patent/FR2622192A1/fr active Granted
- 1988-10-21 IT IT8822399A patent/IT1230592B/it active
- 1988-10-21 CH CH3921/88A patent/CH676715A5/de not_active IP Right Cessation
- 1988-10-21 NL NL8802595A patent/NL8802595A/nl active Search and Examination
- 1988-10-21 DE DE3836006A patent/DE3836006C2/de not_active Expired - Lifetime
- 1988-10-22 JP JP63-265285A patent/JPH075623B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01146891A (ja) | 1989-06-08 |
| CH676715A5 (enExample) | 1991-02-28 |
| FR2622192A1 (fr) | 1989-04-28 |
| GB8824330D0 (en) | 1988-11-23 |
| IT8822399A0 (it) | 1988-10-21 |
| FR2622192B1 (enExample) | 1994-11-10 |
| GB2211502A (en) | 1989-07-05 |
| CA1308711C (en) | 1992-10-13 |
| US4987237A (en) | 1991-01-22 |
| GB2211502B (en) | 1992-02-19 |
| IT1230592B (it) | 1991-10-28 |
| BE1003250A5 (fr) | 1992-02-11 |
| JPH075623B2 (ja) | 1995-01-25 |
| JPH075623B1 (enExample) | 1995-01-25 |
| DE3836006A1 (de) | 1989-05-03 |
| DE3836006C2 (de) | 1996-07-11 |
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