CS221505B2 - Method of making the compounds of the type of n-acetylmuramyle - Google Patents
Method of making the compounds of the type of n-acetylmuramyle Download PDFInfo
- Publication number
- CS221505B2 CS221505B2 CS793866A CS386679A CS221505B2 CS 221505 B2 CS221505 B2 CS 221505B2 CS 793866 A CS793866 A CS 793866A CS 386679 A CS386679 A CS 386679A CS 221505 B2 CS221505 B2 CS 221505B2
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- CS
- Czechoslovakia
- Prior art keywords
- formula
- group
- dipeptide
- defined above
- compound
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title description 3
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- 108010006232 Neuraminidase Proteins 0.000 description 1
- 102000011931 Nucleoproteins Human genes 0.000 description 1
- 108010061100 Nucleoproteins Proteins 0.000 description 1
- 108010013639 Peptidoglycan Chemical group 0.000 description 1
- 241000139306 Platt Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000125258 Scandix pecten-veneris Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 102000002262 Thromboplastin Human genes 0.000 description 1
- 108010000499 Thromboplastin Proteins 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000000688 bacterial toxin Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- SAKUKAQFBMDKGX-UHFFFAOYSA-N butan-1-ol;2-pyridin-2-ylacetic acid;hydrate Chemical compound O.CCCCO.OC(=O)CC1=CC=CC=N1 SAKUKAQFBMDKGX-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005640 glucopyranosyl group Chemical group 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 230000035931 haemagglutination Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000007124 immune defense Effects 0.000 description 1
- 210000000987 immune system Anatomy 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
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AVAJWZFDBWICHC-NTSWFWBYSA-N methyl (2R)-5-amino-2-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoate Chemical compound COC([C@H](NC([C@@H](N)C)=O)CCC(N)=O)=O AVAJWZFDBWICHC-NTSWFWBYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000002947 procoagulating effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical class [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000008494 α-glucosides Chemical class 0.000 description 1
- 150000008495 β-glucosides Chemical class 0.000 description 1
Classifications
-
- 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
- C07K9/005—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 containing within the molecule the substructure with m, n > 0 and m+n > 0, A, B, D, E being heteroatoms; X being a bond or a chain, e.g. muramylpeptides
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
-
- 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
- A61K2039/5555—Muramyl dipeptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Microbiology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Mycology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dispersion Chemistry (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7816793A FR2428051A1 (fr) | 1978-06-05 | 1978-06-05 | Nouveaux composes du type muramyl-peptide et medicaments les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS221505B2 true CS221505B2 (en) | 1983-04-29 |
Family
ID=9209095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS793866A CS221505B2 (en) | 1978-06-05 | 1979-06-05 | Method of making the compounds of the type of n-acetylmuramyle |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4693998A (enExample) |
| EP (1) | EP0006068B1 (enExample) |
| JP (1) | JPS55392A (enExample) |
| AR (1) | AR228240A1 (enExample) |
| AT (1) | ATE4719T1 (enExample) |
| AU (1) | AU536516B2 (enExample) |
| CA (1) | CA1249700A (enExample) |
| CS (1) | CS221505B2 (enExample) |
| DD (1) | DD145274A5 (enExample) |
| DE (1) | DE2966178D1 (enExample) |
| DK (1) | DK150147C (enExample) |
| EG (1) | EG14154A (enExample) |
| ES (1) | ES481785A1 (enExample) |
| FR (1) | FR2428051A1 (enExample) |
| HU (1) | HU184041B (enExample) |
| IL (1) | IL57476A (enExample) |
| MA (1) | MA18474A1 (enExample) |
| OA (1) | OA06274A (enExample) |
| PL (1) | PL123483B1 (enExample) |
| PT (1) | PT69725A (enExample) |
| SU (2) | SU1326197A3 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4368190A (en) * | 1980-04-17 | 1983-01-11 | Merck & Co., Inc. | Immunologically active dipeptidyl 4-O-,6-O-acyl-2-amino-2-deoxy-D-glucose derivatives and methods for their preparation |
| JPS5784223A (en) * | 1980-11-13 | 1982-05-26 | Nissan Motor Co Ltd | Vibration absorber of vehicle |
| FR2529463B1 (fr) * | 1982-07-05 | 1986-01-10 | Centre Nat Rech Scient | Procede et dispositif pour l'encapsulation dans les erythrocytes d'au moins une substance a activite biologique, notamment des effecteurs allosteriques de l'hemoglobine et erythrocytes ainsi obtenus |
| FI79330C (fi) * | 1982-07-23 | 1989-12-11 | Ciba Geigy Ag | Foerfarande foer framstaellning av farmakologiskt verkande muramylpeptid-n-(2-fosfatidyloxietyl)-amider. |
| US5134230A (en) * | 1988-03-02 | 1992-07-28 | Daiichi Pharmaceutical Co., Ltd. | 2-Deoxy-2-aminoglucopyranoside derivatives |
| HU212924B (en) * | 1989-05-25 | 1996-12-30 | Chiron Corp | Adjuvant formulation comprising a submicron oil droplet emulsion |
| WO2000068251A1 (en) | 1999-05-07 | 2000-11-16 | The University Of Virginia Patent Foundation | Biological production of stable glutamine, poly-glutamine derivatives in transgenic organisms and their use for therapeutic purposes |
| CN109406709B (zh) * | 2018-12-27 | 2020-11-10 | 福建省中医药研究院(福建省青草药开发服务中心） | 一种太子参药材中氨基酸类成分的薄层鉴别方法 |
| BR112022019202A2 (pt) * | 2020-03-26 | 2022-11-08 | Nutrivert Llc | Oligopeptídeo, composição farmacêutica, composição, e, método para reduzir a inflamação intestinal em um ser humano, para promover crescimento em um animal e para realçar conversão de alimento em um animal |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2292486A1 (fr) * | 1974-07-01 | 1976-06-25 | Anvar | Adjuvants immunologiques solubles dans l'eau, notamment pour vaccins, obtenus a partir de microbacteries et autres micro-organismes |
| CH613709A5 (en) * | 1975-12-10 | 1979-10-15 | Ciba Geigy Ag | Process for the preparation of glucosamine derivatives |
| GB1573126A (en) * | 1976-03-10 | 1980-08-13 | Anvar | Immunising and anti-infectious adjuvant agents comprising peptide derivatives of muramic acid |
| US4153684A (en) * | 1976-03-10 | 1979-05-08 | Agence Nationale De Valorisation De La Recherche (Anvar) | Immunizing and anti-infectious adjuvant agents constituted by N-acetyl-muramyl-L-alanyl-D-glutamic acid derivatives |
| FR2369292A1 (fr) * | 1976-11-02 | 1978-05-26 | Anvar | Agents adjuvants immunit |
| FR2355505A1 (fr) * | 1976-06-24 | 1978-01-20 | Anvar | Nouvel agent adjuvant immunitaire |
| FR2358159A1 (fr) * | 1976-07-16 | 1978-02-10 | Anvar | Le diamide de l'acide 2-(2-acetamido-2-deoxy-3 - o-d-glucopyranosyl) - d-propionyl-l-alanyl-d-glutamique et medicaments le contenant |
| FR2368282A1 (fr) * | 1976-10-22 | 1978-05-19 | Anvar | Adjuvant immunologique constitue par le p-amino-phenyl de n-acetyl-muramyl-l-alanyl-d-isoglutamine |
| FI66878C (fi) * | 1978-02-24 | 1984-12-10 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya antigenderivat |
-
1978
- 1978-06-05 FR FR7816793A patent/FR2428051A1/fr active Granted
-
1979
- 1979-06-01 DK DK229479A patent/DK150147C/da not_active IP Right Cessation
- 1979-06-01 AT AT79400357T patent/ATE4719T1/de not_active IP Right Cessation
- 1979-06-01 DE DE7979400357T patent/DE2966178D1/de not_active Expired
- 1979-06-01 EP EP79400357A patent/EP0006068B1/fr not_active Expired
- 1979-06-04 EG EG342/79A patent/EG14154A/xx active
- 1979-06-04 AR AR276790A patent/AR228240A1/es active
- 1979-06-05 CA CA000329122A patent/CA1249700A/en not_active Expired
- 1979-06-05 AU AU47756/79A patent/AU536516B2/en not_active Ceased
- 1979-06-05 JP JP6953179A patent/JPS55392A/ja active Granted
- 1979-06-05 DD DD79213401A patent/DD145274A5/de unknown
- 1979-06-05 CS CS793866A patent/CS221505B2/cs unknown
- 1979-06-05 HU HU79AA933A patent/HU184041B/hu not_active IP Right Cessation
- 1979-06-05 MA MA18668A patent/MA18474A1/fr unknown
- 1979-06-05 OA OA56827A patent/OA06274A/xx unknown
- 1979-06-05 IL IL57476A patent/IL57476A/xx unknown
- 1979-06-05 SU SU792777850A patent/SU1326197A3/ru active
- 1979-06-05 ES ES481785A patent/ES481785A1/es not_active Expired
- 1979-06-05 PT PT69725A patent/PT69725A/pt unknown
- 1979-06-05 PL PL1979216102A patent/PL123483B1/pl unknown
-
1982
- 1982-11-30 SU SU823516804A patent/SU1346046A3/ru active
-
1985
- 1985-11-07 US US06/797,771 patent/US4693998A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU536516B2 (en) | 1984-05-10 |
| ES481785A1 (es) | 1980-02-16 |
| EP0006068A3 (en) | 1980-01-09 |
| DK150147C (da) | 1988-01-18 |
| FR2428051A1 (fr) | 1980-01-04 |
| JPH0233720B2 (enExample) | 1990-07-30 |
| JPS55392A (en) | 1980-01-05 |
| PL123483B1 (en) | 1982-10-30 |
| OA06274A (fr) | 1981-06-30 |
| PT69725A (fr) | 1979-07-01 |
| AR228240A1 (es) | 1983-02-15 |
| IL57476A0 (en) | 1979-10-31 |
| SU1326197A3 (ru) | 1987-07-23 |
| SU1346046A3 (ru) | 1987-10-15 |
| HU184041B (en) | 1984-06-28 |
| FR2428051B1 (enExample) | 1981-12-04 |
| EP0006068A2 (fr) | 1979-12-12 |
| MA18474A1 (fr) | 1979-12-31 |
| EG14154A (en) | 1983-09-30 |
| DE2966178D1 (en) | 1983-10-27 |
| EP0006068B1 (fr) | 1983-09-21 |
| DD145274A5 (de) | 1980-12-03 |
| DK150147B (da) | 1986-12-15 |
| IL57476A (en) | 1984-06-29 |
| PL216102A1 (enExample) | 1980-03-24 |
| ATE4719T1 (de) | 1983-10-15 |
| AU4775679A (en) | 1979-12-13 |
| DK229479A (da) | 1979-12-06 |
| CA1249700A (en) | 1989-01-31 |
| US4693998A (en) | 1987-09-15 |
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