BE1003250A5 - Derives du monophosphoryllipide a et leur preparation. - Google Patents
Derives du monophosphoryllipide a et leur preparation. Download PDFInfo
- Publication number
- BE1003250A5 BE1003250A5 BE8801207A BE8801207A BE1003250A5 BE 1003250 A5 BE1003250 A5 BE 1003250A5 BE 8801207 A BE8801207 A BE 8801207A BE 8801207 A BE8801207 A BE 8801207A BE 1003250 A5 BE1003250 A5 BE 1003250A5
- Authority
- BE
- Belgium
- Prior art keywords
- derivatives
- monophosphoryllipid
- preparation
- lipid
- radicals
- Prior art date
Links
- 229940035032 monophosphoryl lipid a Drugs 0.000 title 1
- 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 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000011149 active material Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 239000007822 coupling agent Substances 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 230000003308 immunostimulating effect Effects 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 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)
Abstract
L'invention concerne de nouveaux dérivés du monophoshoryllipide A et un procédé de préparation de celui-ci. Les dérivés contiennent un ou plusieurs radicaux libres, comme les radicaux amine, sur une chaîne latérale attachée aux radicaux hydroxyle primaires du noyau monophosphoryllipide A par l'intermédiaire d'un radical ester. Les dérivés en question fournissent un procédé commode de couplage du lipide A par l'intermédiaire d'agents de couplage à divers matériaux et substrats biologiquement actifs, où l'on souhaite voir apparaître les propriétés immunostimulantes du lipide A.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/112,742 US4987237A (en) | 1983-08-26 | 1987-10-22 | Derivatives of monophosphoryl lipid A |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE1003250A5 true BE1003250A5 (fr) | 1992-02-11 |
Family
ID=22345625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE8801207A BE1003250A5 (fr) | 1987-10-22 | 1988-10-20 | Derives du monophosphoryllipide a et leur preparation. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4987237A (fr) |
| JP (1) | JPH075623B2 (fr) |
| BE (1) | BE1003250A5 (fr) |
| CA (1) | CA1308711C (fr) |
| CH (1) | CH676715A5 (fr) |
| DE (1) | DE3836006C2 (fr) |
| FR (1) | FR2622192A1 (fr) |
| GB (1) | GB2211502B (fr) |
| IT (1) | IT1230592B (fr) |
| NL (1) | NL8802595A (fr) |
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 |
| EP0482068A1 (fr) * | 1989-07-14 | 1992-04-29 | American Cyanamid Company | Cytokine et supports d'hormone pour vaccins conjugues |
| US5498708A (en) * | 1989-07-18 | 1996-03-12 | Montefiore Medical Center | Method of synthesizing polyesters |
| WO1991016332A1 (fr) * | 1990-04-12 | 1991-10-31 | Japan Tobacco Inc. | Derive de 4,6-o-hydroxyphosphorylglucosamine |
| 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 |
| HU230847B1 (en) | 2000-05-19 | 2018-08-28 | Corixa Corp | Prophylactic and therapeutic treatment of infectious and other diseases with mono and disaccharide-based compounds |
| 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 |
| KR100885008B1 (ko) * | 2002-02-04 | 2009-02-20 | 코릭사 코포레이션 | 신규 면역효과기 화합물 |
| WO2003073827A2 (fr) * | 2002-02-28 | 2003-09-12 | Corixa Corporation | Procede de modulation de cellules dendritiques a l'aide d'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 |
| ES2456066T3 (es) | 2002-07-08 | 2014-04-21 | Corixa Corporation | Procesos para la producción de fosfato de aminoalquil glucosaminida e inmunoefectores disacáridos, e intermedios para ello |
| KR101110889B1 (ko) | 2003-01-06 | 2012-02-20 | 코릭사 코포레이션 | 특정의 아미노알킬 글루코사미나이드 포스페이트 화합물 및그들의 용도 |
| US7960522B2 (en) | 2003-01-06 | 2011-06-14 | Corixa Corporation | Certain aminoalkyl glucosaminide phosphate compounds and their use |
| DE60304989T2 (de) * | 2003-02-18 | 2007-03-29 | Clinique La Prairie Research S.A. | Zusammensetzungen enthaltend fötales Hämoglobin und bakterielles Endotoxin und fakultativ zusätzliche fötale Leberkomponenten |
| WO2006073921A2 (fr) * | 2004-12-30 | 2006-07-13 | The Rockefeller University | Compositions et procedes permettant de renforcer la maturation et la fonction de cellules dendritiques |
| 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 |
| EP3403667B1 (fr) | 2006-09-26 | 2020-07-22 | Infectious Disease Research Institute | Composition de vaccin contenant un adjuvant synthétique |
| US20090181078A1 (en) | 2006-09-26 | 2009-07-16 | Infectious Disease Research Institute | Vaccine composition containing synthetic adjuvant |
| HUE025149T2 (hu) | 2007-08-02 | 2016-01-28 | Biondvax Pharmaceuticals Ltd | Multimer multiepitóp influenza vakcinák |
| 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 |
| US8637053B2 (en) | 2007-12-03 | 2014-01-28 | President And Fellows Of Harvard College | Chlamydia antigens |
| SI2437753T1 (sl) | 2009-06-05 | 2016-12-30 | Infectious Disease Research Institute | Sintetični glukopiranozil-lipidni adjuvansi in cepivni sestavki, ki jih vsebujejo |
| AU2011360572B2 (en) | 2011-02-22 | 2017-03-02 | Biondvax Pharmaceuticals Ltd. | Multimeric multiepitope polypeptides in improved seasonal and pandemic influenza vaccines |
| BR112013025799A2 (pt) | 2011-04-08 | 2016-12-20 | Immune Design Corp | método para induzir uma resposta imune em um sujeito, e, preparação |
| GB201106802D0 (en) | 2011-04-21 | 2011-06-01 | Allergy Therapeutics Ltd | Process for preparing vaccine composition |
| EP2850431B1 (fr) | 2012-05-16 | 2018-04-18 | Immune Design Corp. | Vaccins contre le hsv-2 |
| AU2014214844B2 (en) | 2013-02-07 | 2017-12-14 | Children's Medical Center Corporation | Protein antigens that provide protection against pneumococcal colonization and/or disease |
| EP2958935B1 (fr) | 2013-02-20 | 2019-07-03 | Bergen Teknologioverforing AS | Vaccin |
| JP6426706B2 (ja) | 2013-04-18 | 2018-11-21 | イミューン デザイン コーポレイション | がん処置で使用するためのgla単剤療法 |
| US9463198B2 (en) | 2013-06-04 | 2016-10-11 | Infectious Disease Research Institute | Compositions and methods for reducing or preventing metastasis |
| US9919029B2 (en) | 2013-07-26 | 2018-03-20 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods and pharmaceutical compositions for the treatment of bacterial infections |
| WO2016180852A1 (fr) | 2015-05-12 | 2016-11-17 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Procédés de préparation de cellules t spécifiques de l'antigène à partir d'un échantillon de sang de cordon ombilical |
| IL273120B2 (en) | 2017-09-13 | 2023-10-01 | Sanofi Pasteur | A compound that induces an immune response to cytomegalovirus |
| TW201946650A (zh) | 2018-03-12 | 2019-12-16 | 美商詹森藥物公司 | 針對腹內感染之疫苗 |
| CN113195520A (zh) | 2018-08-24 | 2021-07-30 | 挪威西部创新股份有限公司 | 作为抗腹泻疫苗抗原的热稳定肠毒素突变体 |
| KR20220107166A (ko) | 2019-10-02 | 2022-08-02 | 얀센 백신스 앤드 프리벤션 비.브이. | 스타필로코커스 펩티드 및 사용 방법 |
| CN115038461A (zh) | 2020-01-16 | 2022-09-09 | 杨森制药公司 | FimH突变体、其组合物及其用途 |
| TW202241929A (zh) | 2021-01-12 | 2022-11-01 | 美商詹森藥物公司 | FimH突變體、其組成物及其用途 |
| AU2022251305A1 (en) | 2021-04-01 | 2023-09-07 | Janssen Pharmaceuticals, Inc. | Production of e. coli o18 bioconjugates |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0414725Y2 (fr) * | 1980-09-30 | 1992-04-02 | ||
| US4436728A (en) * | 1982-05-26 | 1984-03-13 | Ribi Immunochem Research, Inc. | Refined detoxified endotoxin product |
| US4436727A (en) * | 1982-05-26 | 1984-03-13 | Ribi Immunochem Research, Inc. | Refined detoxified endotoxin product |
-
1987
- 1987-10-22 US US07/112,742 patent/US4987237A/en not_active Expired - Lifetime
-
1988
- 1988-10-14 CA CA000580545A patent/CA1308711C/fr 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 NL NL8802595A patent/NL8802595A/nl active Search and Examination
- 1988-10-21 FR FR8813812A patent/FR2622192A1/fr active Granted
- 1988-10-21 DE DE3836006A patent/DE3836006C2/de not_active Expired - Lifetime
- 1988-10-21 CH CH3921/88A patent/CH676715A5/de not_active IP Right Cessation
- 1988-10-21 IT IT8822399A patent/IT1230592B/it active
- 1988-10-22 JP JP63-265285A patent/JPH075623B2/ja not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Non-Patent Citations (8)
| Title |
|---|
| BIOMEDICAL MASS SPECTROMETRY, vol. 11, no. 3, mars 1984, pages 132-141; U. SEYDEL et al.: "Laser desorption mass spectrometry of synthetic lipid A-like compounds" * |
| CHEMISTRY LETTERS, 1980, pages 1373-1376, Tokyo, JP; M. INAGE et al.: "Chemical synthesis of bisdephospho lipid A of Salmonella endotoxin" * |
| INFECTION AND IMMUNITY, vol. 44, no. 2, mai 1984, pages 421-426, Washington, D.C., US; K.-I. TANAMOTO et al.: "Biological activities of synthetic lipid A analogs; Pyrogenicity lethal toxicity, anticomplement activity, and induction of gelation of Limulus amoebocyte lysate" * |
| PATENT ABSTRACTS OF JAPAN, vol. 11, no. 357 (C-458)[2804], 20 novembre 1987; & JP-A-62 129 293 (TOHO YAKUHIN KOGYO K.K.) 11-06-1987 * |
| PATENT ABSTRACTS OF JAPAN, vol. 12, no. 50 (C-476)[2897], 16 février 1988; & JP-A-62 195 396 (TOHO YAHUKIN KOGYO K.K.) 28-08-1987 * |
| TETRAHEDRON LETTERS, vol. 21, 1980, pages 3889-3892, Oxford, GB; M. INAGE et al.: "Synthesis of lyposaccharide corresponding to fundamental structure of Salmonella-type lipid A" * |
| TETRAHEDRON LETTERS, vol. 22, no. 24, 1981 pages 2281-2284, Oxford, GB; M. INAGE et al.: "Chemical synthesis of phosphorylated fundamental structure of lipid A" * |
| TETRAHEDRON LETTERS, vol. 24, no. 19, 1983, pages 2011-2014, Oxford, GB; M. INAGE et al.: "Synthetic approach to lipid A: Preparation of phosphorylated disaccharides containing (R)-3-hydroxyacyl and (R)-3-acyloxyacyl groups" * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1230592B (it) | 1991-10-28 |
| CA1308711C (fr) | 1992-10-13 |
| JPH075623B2 (ja) | 1995-01-25 |
| DE3836006A1 (de) | 1989-05-03 |
| FR2622192A1 (fr) | 1989-04-28 |
| GB2211502A (en) | 1989-07-05 |
| GB2211502B (en) | 1992-02-19 |
| FR2622192B1 (fr) | 1994-11-10 |
| CH676715A5 (fr) | 1991-02-28 |
| NL8802595A (nl) | 1989-05-16 |
| IT8822399A0 (it) | 1988-10-21 |
| JPH075623B1 (fr) | 1995-01-25 |
| GB8824330D0 (en) | 1988-11-23 |
| US4987237A (en) | 1991-01-22 |
| DE3836006C2 (de) | 1996-07-11 |
| JPH01146891A (ja) | 1989-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE20 | Patent expired |
Owner name: *RIBI IMMUNOCHEM RESEARCH INC. Effective date: 20081020 |