DE2954218C2 - Macrolid-Antibiotika und diese Antibiotika enthaltende pharmazeutische Präparate - Google Patents
Macrolid-Antibiotika und diese Antibiotika enthaltende pharmazeutische PräparateInfo
- Publication number
- DE2954218C2 DE2954218C2 DE2954218A DE2954218A DE2954218C2 DE 2954218 C2 DE2954218 C2 DE 2954218C2 DE 2954218 A DE2954218 A DE 2954218A DE 2954218 A DE2954218 A DE 2954218A DE 2954218 C2 DE2954218 C2 DE 2954218C2
- Authority
- DE
- Germany
- Prior art keywords
- antibiotics
- macrolide
- pharmaceutical preparations
- preparations containing
- methanol
- 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
Links
- 239000003120 macrolide antibiotic agent Substances 0.000 title claims description 26
- 239000003242 anti bacterial agent Substances 0.000 title description 5
- 229940088710 antibiotic agent Drugs 0.000 title description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 241000191967 Staphylococcus aureus Species 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- YRMCBQLZVBXOSJ-PCFSSPOYSA-N (e)-3-[(6r,6as)-4-hydroxy-6-methoxy-3-methyl-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl]prop-2-enamide Chemical compound CO[C@H]1NC2=C(O)C(C)=CC=C2C(=O)N2C=C(\C=C\C(N)=O)C[C@@H]12 YRMCBQLZVBXOSJ-PCFSSPOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- DBTIHDIIXPQOFR-JMHKOBKLSA-N mycinamicin IV Chemical compound O([C@@H]1[C@@H](C)/C=C/C(=O)O[C@@H]([C@H](/C=C/C=C/C(=O)[C@H](C)C[C@@H]1C)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O DBTIHDIIXPQOFR-JMHKOBKLSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- 229910021554 Chromium(II) chloride Inorganic materials 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- 241000193996 Streptococcus pyogenes Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002725 anti-mycoplasma Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940023064 escherichia coli Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QABCJBNUVVMWAL-HXRJSAKRSA-N (2e,5r,7s,8s,9s,10e,14r,15r)-8-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-15-[[(2r,3r,4r,5r,6r)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,7,9-trimethyl-13,17-dioxabicyclo[14.1.0]heptadeca-2,10-diene-4,12-dione Chemical compound O([C@@H]1[C@@H](C)/C=C/C(=O)O[C@@H]([C@H](C2OC2/C=C/C(=O)[C@H](C)C[C@@H]1C)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O QABCJBNUVVMWAL-HXRJSAKRSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000186227 Corynebacterium diphtheriae Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000515012 Micrococcus flavus Species 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 241000204022 Mycoplasma gallisepticum Species 0.000 description 1
- 241000202942 Mycoplasma synoviae Species 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 241000607762 Shigella flexneri Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 241000193985 Streptococcus agalactiae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical group C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003712 glycosamine group Chemical group 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930187734 mycinamicin Natural products 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- -1 sodium carbonate Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000004207 white and yellow bees wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
- C12P1/06—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes by using actinomycetales
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/29—Micromonospora
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/867—Micromonospora
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Polymers & Plastics (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Mycology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Food Science & Technology (AREA)
- Animal Husbandry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5437378A JPS54148701A (en) | 1978-05-10 | 1978-05-10 | Novel macrolide antibiotic, its preparaion and its producing bacteria |
| JP2478879A JPS55115900A (en) | 1979-03-02 | 1979-03-02 | Novel macrolide antibiotic substance a11725 3 and its preparation |
| JP3131679A JPS55122799A (en) | 1979-03-16 | 1979-03-16 | Novel macrolide antibiotic substances a11725 1a and 2a |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2954218C2 true DE2954218C2 (de) | 1986-08-28 |
Family
ID=27284787
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2954218A Expired DE2954218C2 (de) | 1978-05-10 | 1979-05-09 | Macrolid-Antibiotika und diese Antibiotika enthaltende pharmazeutische Präparate |
| DE19792918711 Granted DE2918711A1 (de) | 1978-05-10 | 1979-05-09 | Macrolid-antibiotika, verfahren zu ihrer gewinnung und diese antibiotika enthaltende pharmazeutische praeparate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792918711 Granted DE2918711A1 (de) | 1978-05-10 | 1979-05-09 | Macrolid-antibiotika, verfahren zu ihrer gewinnung und diese antibiotika enthaltende pharmazeutische praeparate |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4291021A (en, 2012) |
| CA (1) | CA1125203A (en, 2012) |
| DE (2) | DE2954218C2 (en, 2012) |
| ES (1) | ES480405A1 (en, 2012) |
| FR (1) | FR2425444A1 (en, 2012) |
| GB (1) | GB2020647B (en, 2012) |
| IT (1) | IT1113372B (en, 2012) |
| NL (1) | NL192621C (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO803356L (no) * | 1979-11-09 | 1981-05-11 | Schering Corp | Fremgangsmaate ved fremstilling av macrolidantibiotika |
| US4367287A (en) * | 1979-11-09 | 1983-01-04 | Schering Corporation | Process of producing antibiotic AR-5 complex |
| US4307085A (en) * | 1979-11-09 | 1981-12-22 | Schering Corporation | Antibiotic AR-5 complex, antibiotics coproduced therewith and derivatives thereof |
| JPH06701B2 (ja) * | 1983-12-01 | 1994-01-05 | 旭化成工業株式会社 | 動物用組成物 |
| JPS6163289A (ja) * | 1984-09-03 | 1986-04-01 | Kyowa Hakko Kogyo Co Ltd | 新規物質ｋ―２５９―２ |
| US4843008A (en) * | 1984-12-24 | 1989-06-27 | Yamanouchi Pharmaceutical Co., Ltd. | Novel microorganisms and a novel process for producing antibiotics |
| JPH0639480B2 (ja) * | 1985-07-16 | 1994-05-25 | 麒麟麦酒株式会社 | 新規マクロライド系抗生物質ｍ１１９ |
| JP2787458B2 (ja) * | 1989-01-20 | 1998-08-20 | 旭化成工業株式会社 | 抗生物質ｌ５３―１８ａおよびその製造法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4723548U (en, 2012) * | 1971-04-09 | 1972-11-16 | ||
| JPS50145588A (en, 2012) * | 1974-05-16 | 1975-11-21 | ||
| US4032631A (en) * | 1975-12-19 | 1977-06-28 | Pfizer Inc. | Mixture of antibiotics produced by new species of micromonospora |
| JPS5849235B2 (ja) * | 1977-03-31 | 1983-11-02 | 協和醗酵工業株式会社 | 新抗生物質ｘｋ−９９およびその製造法 |
-
1979
- 1979-04-26 CA CA326,416A patent/CA1125203A/en not_active Expired
- 1979-05-08 NL NL7903601A patent/NL192621C/nl not_active IP Right Cessation
- 1979-05-08 GB GB7915807A patent/GB2020647B/en not_active Expired
- 1979-05-09 ES ES480405A patent/ES480405A1/es not_active Expired
- 1979-05-09 DE DE2954218A patent/DE2954218C2/de not_active Expired
- 1979-05-09 DE DE19792918711 patent/DE2918711A1/de active Granted
- 1979-05-10 IT IT22536/79A patent/IT1113372B/it active
- 1979-05-10 US US06/037,846 patent/US4291021A/en not_active Expired - Lifetime
- 1979-05-10 FR FR7911883A patent/FR2425444A1/fr active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1113372B (it) | 1986-01-20 |
| NL7903601A (nl) | 1979-11-13 |
| DE2918711A1 (de) | 1979-11-22 |
| FR2425444A1 (fr) | 1979-12-07 |
| GB2020647A (en) | 1979-11-21 |
| DE2918711C2 (en, 2012) | 1987-08-06 |
| FR2425444B1 (en, 2012) | 1983-09-23 |
| GB2020647B (en) | 1982-07-28 |
| NL192621C (nl) | 1997-11-04 |
| ES480405A1 (es) | 1980-01-01 |
| NL192621B (nl) | 1997-07-01 |
| CA1125203A (en) | 1982-06-08 |
| IT7922536A0 (it) | 1979-05-10 |
| US4291021A (en) | 1981-09-22 |
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