CA1211731A - De(mycinosyloxy)tylosin derivatives - Google Patents
De(mycinosyloxy)tylosin derivativesInfo
- Publication number
- CA1211731A CA1211731A CA000431623A CA431623A CA1211731A CA 1211731 A CA1211731 A CA 1211731A CA 000431623 A CA000431623 A CA 000431623A CA 431623 A CA431623 A CA 431623A CA 1211731 A CA1211731 A CA 1211731A
- Authority
- CA
- Canada
- Prior art keywords
- dmot
- deoxo
- mycaminosyltylactone
- tylosin
- medium
- 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
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical class O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 claims abstract description 30
- 241000187438 Streptomyces fradiae Species 0.000 claims abstract description 16
- -1 acyl ester Chemical class 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000004182 Tylosin Substances 0.000 claims abstract description 10
- 229960004059 tylosin Drugs 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 8
- BMKVJAXXBOWJEE-MIFVOYFBSA-N (11e,13e)-6-[4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-7,16-diethyl-4-hydroxy-5,9,13,15-tetramethyl-1-oxacyclohexadeca-11,13-diene-2,10-dione Chemical compound CCC1CC(C)C(=O)\C=C\C(\C)=C\C(C)C(CC)OC(=O)CC(O)C(C)C1OC1C(O)C(N(C)C)C(O)C(C)O1 BMKVJAXXBOWJEE-MIFVOYFBSA-N 0.000 claims abstract description 5
- 230000003115 biocidal effect Effects 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229930194936 Tylosin Natural products 0.000 claims description 9
- 239000001963 growth medium Substances 0.000 claims description 9
- 235000019375 tylosin Nutrition 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229940088710 antibiotic agent Drugs 0.000 claims description 6
- 238000010564 aerobic fermentation Methods 0.000 claims description 4
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229940041033 macrolides Drugs 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000000855 fermentation Methods 0.000 abstract description 14
- 230000004151 fermentation Effects 0.000 abstract description 14
- 239000000543 intermediate Substances 0.000 abstract description 4
- 239000002609 medium Substances 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 108010068370 Glutens Proteins 0.000 description 2
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- 241000204031 Mycoplasma Species 0.000 description 2
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- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
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- 239000008367 deionised water Substances 0.000 description 2
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- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000021312 gluten Nutrition 0.000 description 2
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- 239000000787 lecithin Substances 0.000 description 2
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- 235000013379 molasses Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
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- 235000011007 phosphoric acid Nutrition 0.000 description 2
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- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
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- 235000013619 trace mineral Nutrition 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- ZVOOGERIHVAODX-QWWGUZMMSA-N 2-[(4r,5s,6s,7r,9r,11e,13e,15r,16r)-6-[(2r,3r,4r,5r,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-(hydroxymethyl)-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-d Chemical compound O=CC[C@H]1C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@H](CO)[C@@H](CC)OC(=O)C[C@@H](O)[C@H](C)[C@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1 ZVOOGERIHVAODX-QWWGUZMMSA-N 0.000 description 1
- 229930193246 23-Demycinosyltylosin Natural products 0.000 description 1
- DIOQKPOBSJVSJS-UHFFFAOYSA-N 3,6-Dideoxy-3-dimethylamino-beta-D-glucose Natural products CC1OC(O)C(O)C(N(C)C)C1O DIOQKPOBSJVSJS-UHFFFAOYSA-N 0.000 description 1
- FREZLSIGWNCSOQ-UHFFFAOYSA-N 3-methylbutanoyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC(=O)CC(C)C FREZLSIGWNCSOQ-UHFFFAOYSA-N 0.000 description 1
- WGUJDBLMJBJUQU-VKRLOHBMSA-N 5-O-mycaminosyltylonolide Chemical compound O=CC[C@H]1C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@H](CO)[C@@H](CC)OC(=O)C[C@@H](O)[C@H](C)[C@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O)[C@@H](C)O1 WGUJDBLMJBJUQU-VKRLOHBMSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012807 shake-flask culturing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YJSXTLYNFBFHAT-HJOMEYPASA-N tylactone Chemical compound CC[C@H]1C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@H](C)[C@@H](CC)OC(=O)C[C@@H](O)[C@H](C)[C@H]1O YJSXTLYNFBFHAT-HJOMEYPASA-N 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 230000009105 vegetative growth Effects 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
- 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
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
- C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
-
- 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
- C12R2001/465—Streptomyces
- C12R2001/54—Streptomyces fradiae
-
- 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
- Y10S435/886—Streptomyces
- Y10S435/896—Streptomyces fradiae
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US394,599 | 1982-07-02 | ||
| US06/394,599 US4423148A (en) | 1982-07-02 | 1982-07-02 | Process for producing 20-dihydro-20-deoxy-23-de(mycinosyloxy)tylosin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1211731A true CA1211731A (en) | 1986-09-23 |
Family
ID=23559638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000431623A Expired CA1211731A (en) | 1982-07-02 | 1983-06-30 | De(mycinosyloxy)tylosin derivatives |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4423148A (forum.php) |
| EP (1) | EP0098732B1 (forum.php) |
| JP (1) | JPS5927899A (forum.php) |
| KR (1) | KR860001997B1 (forum.php) |
| AT (1) | ATE18233T1 (forum.php) |
| CA (1) | CA1211731A (forum.php) |
| DE (1) | DE3362287D1 (forum.php) |
| DK (1) | DK307083A (forum.php) |
| GB (1) | GB2122993B (forum.php) |
| GR (1) | GR78600B (forum.php) |
| IL (1) | IL69093A (forum.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117510561A (zh) * | 2023-11-30 | 2024-02-06 | 中国农业科学院饲料研究所 | 一种泰乐菌素衍生物及其制备方法与应用 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL89714A0 (en) * | 1988-03-28 | 1989-09-28 | Lilly Co Eli | Improvements in or relating to the production of 20-deoxotylosin |
| US5698420A (en) | 1995-12-05 | 1997-12-16 | Pfizer Inc. | Preparation of 4-deoxy-O-mycaminosyltylonolide |
| DE60140936D1 (de) * | 2000-04-13 | 2010-02-11 | Biotica Tech Ltd | Glycosylierte hybrid-verbindungen, deren herstellung und verwendung |
| KR100914251B1 (ko) * | 2007-06-27 | 2009-08-26 | 이화여자대학교 산학협력단 | 신규한 올리보실 틸락톤 및 그 제조 방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3178341A (en) * | 1960-06-27 | 1965-04-13 | Lilly Co Eli | Antibiotics tylosin and desmycosin and derivatives thereof |
| BE667952A (forum.php) * | 1964-08-05 | |||
| NL8004922A (nl) | 1979-09-19 | 1981-03-23 | Toyo Jozo Kk | Deformyltylosinederivaten. |
| ZA813578B (en) * | 1980-06-12 | 1983-01-26 | Lilly Co Eli | Macrolide antibiotics |
| US4366247A (en) * | 1980-07-02 | 1982-12-28 | Eli Lilly And Company | Process for preparing tylactone |
| US4299953A (en) * | 1980-07-29 | 1981-11-10 | Eli Lilly And Company | Mycarosyltylactone |
| US4304856A (en) * | 1980-11-10 | 1981-12-08 | Eli Lilly And Company | Process for producing 20-dihydro-20-deoxy-23-demycinosyltylosin |
-
1982
- 1982-07-02 US US06/394,599 patent/US4423148A/en not_active Expired - Fee Related
-
1983
- 1983-06-28 IL IL69093A patent/IL69093A/xx unknown
- 1983-06-29 DE DE8383303747T patent/DE3362287D1/de not_active Expired
- 1983-06-29 EP EP83303747A patent/EP0098732B1/en not_active Expired
- 1983-06-29 GB GB08317593A patent/GB2122993B/en not_active Expired
- 1983-06-29 AT AT83303747T patent/ATE18233T1/de not_active IP Right Cessation
- 1983-06-29 GR GR71802A patent/GR78600B/el unknown
- 1983-06-30 KR KR1019830002977A patent/KR860001997B1/ko not_active Expired
- 1983-06-30 CA CA000431623A patent/CA1211731A/en not_active Expired
- 1983-07-01 JP JP58120909A patent/JPS5927899A/ja active Pending
- 1983-07-01 DK DK307083A patent/DK307083A/da not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117510561A (zh) * | 2023-11-30 | 2024-02-06 | 中国农业科学院饲料研究所 | 一种泰乐菌素衍生物及其制备方法与应用 |
| CN117510561B (zh) * | 2023-11-30 | 2024-04-02 | 中国农业科学院饲料研究所 | 一种泰乐菌素衍生物及其制备方法与应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| GR78600B (forum.php) | 1984-09-27 |
| DE3362287D1 (en) | 1986-04-03 |
| IL69093A (en) | 1986-09-30 |
| US4423148A (en) | 1983-12-27 |
| KR860001997B1 (ko) | 1986-11-12 |
| EP0098732B1 (en) | 1986-02-26 |
| ATE18233T1 (de) | 1986-03-15 |
| JPS5927899A (ja) | 1984-02-14 |
| GB2122993A (en) | 1984-01-25 |
| GB8317593D0 (en) | 1983-08-03 |
| IL69093A0 (en) | 1983-10-31 |
| KR840005489A (ko) | 1984-11-14 |
| EP0098732A1 (en) | 1984-01-18 |
| GB2122993B (en) | 1986-01-29 |
| DK307083A (da) | 1984-01-03 |
| DK307083D0 (da) | 1983-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |