DD145274A5 - Verfahren zur darstellung neuer verbindungen des muramylpeptidtyps - Google Patents
Verfahren zur darstellung neuer verbindungen des muramylpeptidtyps Download PDFInfo
- Publication number
- DD145274A5 DD145274A5 DD79213401A DD21340179A DD145274A5 DD 145274 A5 DD145274 A5 DD 145274A5 DD 79213401 A DD79213401 A DD 79213401A DD 21340179 A DD21340179 A DD 21340179A DD 145274 A5 DD145274 A5 DD 145274A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- radical
- derivative
- glutamine
- item
- alanyl
- Prior art date
Links
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- 238000000034 method Methods 0.000 title claims description 42
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- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
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- 235000013601 eggs Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
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- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010200 folin Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005640 glucopyranosyl group Chemical group 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 239000000185 hemagglutinin Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 230000016784 immunoglobulin production 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
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 230000001861 immunosuppressant effect Effects 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000003520 lipogenic effect Effects 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
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- 230000001404 mediated effect Effects 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- BSOQXXWZTUDTEL-ZUYCGGNHSA-N muramyl dipeptide Chemical compound OC(=O)CC[C@H](C(N)=O)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O BSOQXXWZTUDTEL-ZUYCGGNHSA-N 0.000 description 1
- 125000001801 mycolyl group Chemical group 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
- 230000003448 neutrophilic 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
- STZOTKNJQXZFFR-UHFFFAOYSA-N oxamoylcarbamic acid Chemical compound NC(=O)C(=O)NC(O)=O STZOTKNJQXZFFR-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003689 pubic bone Anatomy 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 238000007070 tosylation reaction Methods 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
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000004383 yellowing Methods 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)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Communicable Diseases (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 |
|---|---|
| DD145274A5 true DD145274A5 (de) | 1980-12-03 |
Family
ID=9209095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79213401A DD145274A5 (de) | 1978-06-05 | 1979-06-05 | Verfahren zur darstellung neuer verbindungen des muramylpeptidtyps |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4693998A (cs) |
| EP (1) | EP0006068B1 (cs) |
| JP (1) | JPS55392A (cs) |
| AR (1) | AR228240A1 (cs) |
| AT (1) | ATE4719T1 (cs) |
| AU (1) | AU536516B2 (cs) |
| CA (1) | CA1249700A (cs) |
| CS (1) | CS221505B2 (cs) |
| DD (1) | DD145274A5 (cs) |
| DE (1) | DE2966178D1 (cs) |
| DK (1) | DK150147C (cs) |
| EG (1) | EG14154A (cs) |
| ES (1) | ES481785A1 (cs) |
| FR (1) | FR2428051A1 (cs) |
| HU (1) | HU184041B (cs) |
| IL (1) | IL57476A (cs) |
| MA (1) | MA18474A1 (cs) |
| OA (1) | OA06274A (cs) |
| PL (1) | PL123483B1 (cs) |
| PT (1) | PT69725A (cs) |
| SU (2) | SU1326197A3 (cs) |
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 |
| ATE23536T1 (de) * | 1982-07-23 | 1986-11-15 | Ciba Geigy Ag | Neue muramylpeptide und verfahren zu ihrer herstellung. |
| US5134230A (en) * | 1988-03-02 | 1992-07-28 | Daiichi Pharmaceutical Co., Ltd. | 2-Deoxy-2-aminoglucopyranoside derivatives |
| JPH0832638B2 (ja) * | 1989-05-25 | 1996-03-29 | カイロン コーポレイション | サブミクロン油滴乳剤を含んで成るアジュバント製剤 |
| AU4251300A (en) | 1999-05-07 | 2000-11-21 | 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 |
| KR20220158773A (ko) * | 2020-03-26 | 2022-12-01 | 뉴트리버트 엘엘씨 | 항염증 및 성장 촉진 활성을 갖는 데스아세틸글루코사민 무라밀 디펩티드의 친지성 거울상이성질체 |
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 |
| CA1138436A (en) * | 1978-02-24 | 1982-12-28 | Gerhard Baschang | Process for the manufacture of novel antigens |
-
1978
- 1978-06-05 FR FR7816793A patent/FR2428051A1/fr active Granted
-
1979
- 1979-06-01 EP EP79400357A patent/EP0006068B1/fr not_active Expired
- 1979-06-01 DE DE7979400357T patent/DE2966178D1/de not_active Expired
- 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
- 1979-06-04 AR AR276790A patent/AR228240A1/es active
- 1979-06-04 EG EG342/79A patent/EG14154A/xx active
- 1979-06-05 PT PT69725A patent/PT69725A/pt unknown
- 1979-06-05 SU SU792777850A patent/SU1326197A3/ru active
- 1979-06-05 PL PL1979216102A patent/PL123483B1/pl unknown
- 1979-06-05 CS CS793866A patent/CS221505B2/cs unknown
- 1979-06-05 IL IL57476A patent/IL57476A/xx unknown
- 1979-06-05 AU AU47756/79A patent/AU536516B2/en not_active Ceased
- 1979-06-05 ES ES481785A patent/ES481785A1/es not_active Expired
- 1979-06-05 DD DD79213401A patent/DD145274A5/de unknown
- 1979-06-05 CA CA000329122A patent/CA1249700A/en not_active Expired
- 1979-06-05 HU HU79AA933A patent/HU184041B/hu not_active IP Right Cessation
- 1979-06-05 JP JP6953179A patent/JPS55392A/ja active Granted
- 1979-06-05 MA MA18668A patent/MA18474A1/fr unknown
- 1979-06-05 OA OA56827A patent/OA06274A/xx 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 |
|---|---|
| EG14154A (en) | 1983-09-30 |
| FR2428051B1 (cs) | 1981-12-04 |
| DK150147C (da) | 1988-01-18 |
| MA18474A1 (fr) | 1979-12-31 |
| SU1326197A3 (ru) | 1987-07-23 |
| JPS55392A (en) | 1980-01-05 |
| ATE4719T1 (de) | 1983-10-15 |
| CS221505B2 (en) | 1983-04-29 |
| IL57476A (en) | 1984-06-29 |
| SU1346046A3 (ru) | 1987-10-15 |
| HU184041B (en) | 1984-06-28 |
| OA06274A (fr) | 1981-06-30 |
| JPH0233720B2 (cs) | 1990-07-30 |
| US4693998A (en) | 1987-09-15 |
| CA1249700A (en) | 1989-01-31 |
| ES481785A1 (es) | 1980-02-16 |
| DK150147B (da) | 1986-12-15 |
| EP0006068A2 (fr) | 1979-12-12 |
| PL123483B1 (en) | 1982-10-30 |
| DE2966178D1 (en) | 1983-10-27 |
| AU536516B2 (en) | 1984-05-10 |
| FR2428051A1 (fr) | 1980-01-04 |
| DK229479A (da) | 1979-12-06 |
| IL57476A0 (en) | 1979-10-31 |
| PL216102A1 (cs) | 1980-03-24 |
| AU4775679A (en) | 1979-12-13 |
| AR228240A1 (es) | 1983-02-15 |
| EP0006068B1 (fr) | 1983-09-21 |
| PT69725A (fr) | 1979-07-01 |
| EP0006068A3 (en) | 1980-01-09 |
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