CA1308711C - Derivatives of monophosphoryl lipid a and process for preparation - Google Patents
Derivatives of monophosphoryl lipid a and process for preparationInfo
- Publication number
- CA1308711C CA1308711C CA000580545A CA580545A CA1308711C CA 1308711 C CA1308711 C CA 1308711C CA 000580545 A CA000580545 A CA 000580545A CA 580545 A CA580545 A CA 580545A CA 1308711 C CA1308711 C CA 1308711C
- Authority
- CA
- Canada
- Prior art keywords
- mpl
- derivative
- monophosphoryl lipid
- derivatives
- alpha
- 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 - Lifetime
Links
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- 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 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
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- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
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- 229940043376 ammonium acetate Drugs 0.000 description 1
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- 230000000890 antigenic effect Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
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- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
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- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000004520 cell wall skeleton Anatomy 0.000 description 1
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- 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
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
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- 229940047124 interferons Drugs 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
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- 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
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 230000001225 therapeutic effect Effects 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- 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
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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
- 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 |
|---|---|---|---|
| US07/112,742 US4987237A (en) | 1983-08-26 | 1987-10-22 | Derivatives of monophosphoryl lipid A |
| US112,742 | 1987-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1308711C true CA1308711C (en) | 1992-10-13 |
Family
ID=22345625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000580545A Expired - Lifetime CA1308711C (en) | 1987-10-22 | 1988-10-14 | Derivatives of monophosphoryl lipid a and process for preparation |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4987237A (show.php) |
| JP (1) | JPH075623B2 (show.php) |
| BE (1) | BE1003250A5 (show.php) |
| CA (1) | CA1308711C (show.php) |
| CH (1) | CH676715A5 (show.php) |
| DE (1) | DE3836006C2 (show.php) |
| FR (1) | FR2622192A1 (show.php) |
| GB (1) | GB2211502B (show.php) |
| IT (1) | IT1230592B (show.php) |
| NL (1) | NL8802595A (show.php) |
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 |
| AU651949B2 (en) * | 1989-07-14 | 1994-08-11 | 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 |
| US5278300A (en) * | 1990-04-12 | 1994-01-11 | Japan Tobacco, Inc. | 4,6-o-hydroxyphosphoryl-glucosamine derivatives |
| 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 |
| EP1284740B1 (en) | 2000-05-19 | 2008-05-21 | Corixa Corporation | Prophylactic and therapeutic treatment of infectious, autoimmune and allergic diseases with monosaccharide-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 |
| US20030175863A1 (en) * | 2001-08-15 | 2003-09-18 | Birkett Ashley J. | Influenza immunogen and vaccine |
| US7361352B2 (en) * | 2001-08-15 | 2008-04-22 | Acambis, Inc. | Influenza immunogen and vaccine |
| CA2474398A1 (en) * | 2002-02-04 | 2003-08-14 | Corixa Corporation | New immunoeffector compounds |
| US6911434B2 (en) * | 2002-02-04 | 2005-06-28 | Corixa Corporation | Prophylactic and therapeutic treatment of infectious and other diseases with immunoeffector compounds |
| US20040033213A1 (en) * | 2002-02-28 | 2004-02-19 | 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 |
| IL166178A0 (en) | 2002-07-08 | 2006-01-15 | Corixa Corp | Processes for the production of aminoalkyl glucosaminide phosphate and disaccharide immunoeffectors and intermediates therefor |
| US7960522B2 (en) | 2003-01-06 | 2011-06-14 | Corixa Corporation | Certain aminoalkyl glucosaminide phosphate compounds and their use |
| ES2556970T3 (es) | 2003-01-06 | 2016-01-21 | Corixa Corporation | Ciertos compuestos de fosfato de aminoalquil glucosaminida y sus usos |
| DK1449535T3 (da) * | 2003-02-18 | 2006-09-11 | Clinique La Prairie Res Sa | Præparater der omfatter fötalt hæmoglobin og bakterieendotoksin samt eventuelt fötale leverbestanddele |
| 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 |
| SI2068918T2 (sl) * | 2006-09-26 | 2024-10-30 | Access To Advanced Health Institute | Sestavek za cepljenje, ki vsebuje sintetična pomagala |
| US20090181078A1 (en) * | 2006-09-26 | 2009-07-16 | Infectious Disease Research Institute | Vaccine composition containing synthetic adjuvant |
| PL2173376T3 (pl) | 2007-08-02 | 2015-08-31 | Biondvax Pharmaceuticals Ltd | Multimeryczne wieloepitopowe szczepionki przeciwko grypie |
| US20090215908A1 (en) * | 2007-09-24 | 2009-08-27 | Reliance Life Sciences Pvt. Ltd. | Toll like receptor (tlr) signaling antagonist |
| US20090215710A1 (en) * | 2007-09-24 | 2009-08-27 | Reliance Life Sciences Pvt. Ltd. | Carbohydrate based toll-like receptor (tlr) antagonists |
| CA2744739A1 (en) | 2007-12-03 | 2009-06-11 | President And Fellows Of Harvard College | Chlamydia antigens |
| PT2437753T (pt) | 2009-06-05 | 2016-11-23 | Infectious Disease Res Inst | Adjuvantes lipídicos de glucopiranosilo sintéticos e composições de vacina contendo os mesmos |
| US9303070B2 (en) | 2011-02-22 | 2016-04-05 | Biondvax Pharmaceuticals Ltd. | Multimeric multiepitope polypeptides in improved seasonal and pandemic influenza vaccines |
| US9044420B2 (en) | 2011-04-08 | 2015-06-02 | 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 |
| NZ701881A (en) | 2012-05-16 | 2016-10-28 | Immune Design Corp | Vaccines for hsv-2 |
| US11576958B2 (en) | 2013-02-07 | 2023-02-14 | Children's Medical Center Corporation | Protein antigens that provide protection against pneumococcal colonization and/or disease |
| EP2958935B1 (en) | 2013-02-20 | 2019-07-03 | Bergen Teknologioverforing AS | Vaccine |
| EP2986303B1 (en) | 2013-04-18 | 2020-02-26 | 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 |
| EP3632458B1 (en) | 2013-07-26 | 2025-03-19 | INSERM (Institut National de la Santé et de la Recherche Médicale) | 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 |
| BR112020004747A2 (pt) | 2017-09-13 | 2020-09-24 | Sanofi Pasteur | composição imunogênica de citomegalovírus humano |
| WO2019175145A1 (en) | 2018-03-12 | 2019-09-19 | Janssen Vaccines & Prevention B.V. | Vaccines against urinary tract infections |
| 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 |
| CN115151559A (zh) | 2019-10-02 | 2022-10-04 | 扬森疫苗与预防公司 | 葡萄球菌肽和使用方法 |
| PT4090363T (pt) | 2020-01-16 | 2024-09-19 | Janssen Pharmaceuticals Inc | Mutante de fimh, composições com o mesmo e sua utilização |
| 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 |
| MX2023011697A (es) | 2021-04-01 | 2023-10-19 | Janssen Pharmaceuticals Inc | Produccion de bioconjugados o18 de e. coli. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0414725Y2 (show.php) * | 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 |
| 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 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
- 1988-10-21 IT IT8822399A patent/IT1230592B/it active
- 1988-10-21 FR FR8813812A patent/FR2622192A1/fr active Granted
- 1988-10-22 JP JP63-265285A patent/JPH075623B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3836006C2 (de) | 1996-07-11 |
| GB2211502A (en) | 1989-07-05 |
| DE3836006A1 (de) | 1989-05-03 |
| GB8824330D0 (en) | 1988-11-23 |
| CH676715A5 (show.php) | 1991-02-28 |
| NL8802595A (nl) | 1989-05-16 |
| FR2622192B1 (show.php) | 1994-11-10 |
| JPH01146891A (ja) | 1989-06-08 |
| IT1230592B (it) | 1991-10-28 |
| GB2211502B (en) | 1992-02-19 |
| US4987237A (en) | 1991-01-22 |
| IT8822399A0 (it) | 1988-10-21 |
| JPH075623B1 (show.php) | 1995-01-25 |
| BE1003250A5 (fr) | 1992-02-11 |
| JPH075623B2 (ja) | 1995-01-25 |
| FR2622192A1 (fr) | 1989-04-28 |
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