HU194268B - Process for production of derivatives of o-mycaminosile tilonolid esther - Google Patents
Process for production of derivatives of o-mycaminosile tilonolid esther Download PDFInfo
- Publication number
- HU194268B HU194268B HU824016A HU401682A HU194268B HU 194268 B HU194268 B HU 194268B HU 824016 A HU824016 A HU 824016A HU 401682 A HU401682 A HU 401682A HU 194268 B HU194268 B HU 194268B
- Authority
- HU
- Hungary
- Prior art keywords
- acid
- mycaminosyl
- acetyl
- thylonolide
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 phenylacetyl Chemical group 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims description 39
- 238000002360 preparation method Methods 0.000 claims description 15
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 8
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 4
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 4
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 claims description 2
- 229950007593 homonicotinic acid Drugs 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims 2
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 21
- 239000002253 acid Substances 0.000 abstract description 16
- 150000003839 salts Chemical class 0.000 abstract description 12
- 239000003242 anti bacterial agent Substances 0.000 abstract description 8
- 229940088710 antibiotic agent Drugs 0.000 abstract description 7
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 49
- 239000004182 Tylosin Substances 0.000 description 31
- 239000002904 solvent Substances 0.000 description 31
- 229960004059 tylosin Drugs 0.000 description 31
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound 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 description 30
- 229930194936 Tylosin Natural products 0.000 description 29
- 235000019375 tylosin Nutrition 0.000 description 29
- 239000000203 mixture Substances 0.000 description 23
- 239000002609 medium Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000004809 thin layer chromatography Methods 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- XMEGXHDYCSUOJC-KXOLBLKYSA-N 2-[(4r,5s,6s,7r,9r,11e,13e,15r,16r)-16-ethyl-4,6-dihydroxy-15-(hydroxymethyl)-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde Chemical compound CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[C@@H](O)[C@@H](CC=O)C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@@H]1CO XMEGXHDYCSUOJC-KXOLBLKYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- XMEGXHDYCSUOJC-UHFFFAOYSA-N Tylonolide Natural products CCC1OC(=O)CC(O)C(C)C(O)C(CC=O)CC(C)C(=O)C=CC(=CC1CO)C XMEGXHDYCSUOJC-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 150000001793 charged compounds Chemical class 0.000 description 11
- 238000001819 mass spectrum Methods 0.000 description 11
- 241000606860 Pasteurella Species 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 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 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 241000192125 Firmicutes Species 0.000 description 5
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000187438 Streptomyces fradiae Species 0.000 description 4
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- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
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- 241000287828 Gallus gallus Species 0.000 description 3
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- 241001293418 Mannheimia haemolytica Species 0.000 description 3
- YQLFLCVNXSPEKQ-UHFFFAOYSA-N Mycarose Natural products CC1OC(O)CC(C)(O)C1O YQLFLCVNXSPEKQ-UHFFFAOYSA-N 0.000 description 3
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- JYAQWANEOPJVEY-LYFYHCNISA-N mycarose Chemical compound C[C@H](O)[C@H](O)[C@](C)(O)CC=O JYAQWANEOPJVEY-LYFYHCNISA-N 0.000 description 3
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- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
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- 235000014655 lactic acid Nutrition 0.000 description 1
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- 229940067606 lecithin Drugs 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
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- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 1
- 235000007708 morin Nutrition 0.000 description 1
- 229940048991 mycamine Drugs 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- 239000003279 phenylacetic acid Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/330,341 US4401660A (en) | 1981-12-14 | 1981-12-14 | Ester derivatives of 5-O-mycaminosyl tylonolide and method of using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU194268B true HU194268B (en) | 1988-01-28 |
Family
ID=23289335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU824016A HU194268B (en) | 1981-12-14 | 1982-12-13 | Process for production of derivatives of o-mycaminosile tilonolid esther |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4401660A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0082003B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS58110598A (cg-RX-API-DMAC7.html) |
| KR (1) | KR850000978B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1189503A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3268461D1 (cg-RX-API-DMAC7.html) |
| DK (2) | DK153794C (cg-RX-API-DMAC7.html) |
| GB (1) | GB2111497B (cg-RX-API-DMAC7.html) |
| GR (1) | GR77094B (cg-RX-API-DMAC7.html) |
| HU (1) | HU194268B (cg-RX-API-DMAC7.html) |
| IE (1) | IE54283B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL67452A (cg-RX-API-DMAC7.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU551142B2 (en) * | 1981-07-09 | 1986-04-17 | Zaidan Hojin Biseibutsu Kagaku Kenkyukai | Tylosin derivatives |
| CA1196915A (en) * | 1982-01-22 | 1985-11-19 | Hideo Sakakibara | 23-0-acyl-23-demycinosyldesmycosin |
| US4443436A (en) | 1982-09-13 | 1984-04-17 | Eli Lilly And Company | C-20-Modified macrolide derivatives of the macrolide antibiotics tylosin, desmycosin, macrocin, and lactenocin |
| US4629786A (en) * | 1983-02-28 | 1986-12-16 | Eli Lilly And Company | C-20- and C-23 modified macrolide derivatives |
| GB8333624D0 (en) * | 1983-12-16 | 1984-01-25 | Lepetit Spa | Antibiotics l 17054 and l 17392 |
| US4576931A (en) * | 1985-04-03 | 1986-03-18 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai (Microbial Chemistry Research Foundation) | 23-C-Substituted mycaminosyl tylonolide, pharmaceutical compositions and method of use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE667952A (cg-RX-API-DMAC7.html) * | 1964-08-05 | |||
| CH619267A5 (cg-RX-API-DMAC7.html) * | 1975-08-01 | 1980-09-15 | Sanraku Ocean Co | |
| US4321362A (en) * | 1980-06-12 | 1982-03-23 | Eli Lilly And Company | De(mycinosyloxy)tylosin and process for its production |
| US4438109A (en) * | 1980-07-25 | 1984-03-20 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Tylosin derivatives |
| US4299953A (en) * | 1980-07-29 | 1981-11-10 | Eli Lilly And Company | Mycarosyltylactone |
-
1981
- 1981-12-14 US US06/330,341 patent/US4401660A/en not_active Expired - Fee Related
-
1982
- 1982-12-07 CA CA000417149A patent/CA1189503A/en not_active Expired
- 1982-12-10 IL IL67452A patent/IL67452A/xx unknown
- 1982-12-13 IE IE2952/82A patent/IE54283B1/en unknown
- 1982-12-13 EP EP82306635A patent/EP0082003B1/en not_active Expired
- 1982-12-13 DE DE8282306635T patent/DE3268461D1/de not_active Expired
- 1982-12-13 HU HU824016A patent/HU194268B/hu not_active IP Right Cessation
- 1982-12-13 JP JP57219141A patent/JPS58110598A/ja active Pending
- 1982-12-13 DK DK553982A patent/DK153794C/da not_active IP Right Cessation
- 1982-12-13 GB GB08235478A patent/GB2111497B/en not_active Expired
- 1982-12-14 KR KR8205595A patent/KR850000978B1/ko not_active Expired
- 1982-12-14 GR GR70068A patent/GR77094B/el unknown
-
1986
- 1986-12-22 DK DK623786A patent/DK623786A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IE822952L (en) | 1983-06-14 |
| DK553982A (da) | 1983-06-15 |
| GB2111497B (en) | 1985-10-30 |
| GR77094B (cg-RX-API-DMAC7.html) | 1984-09-06 |
| EP0082003A1 (en) | 1983-06-22 |
| DK153794B (da) | 1988-09-05 |
| DK623786D0 (da) | 1986-12-22 |
| CA1189503A (en) | 1985-06-25 |
| DK153794C (da) | 1989-02-20 |
| DE3268461D1 (de) | 1986-02-20 |
| US4401660A (en) | 1983-08-30 |
| DK623786A (da) | 1986-12-22 |
| IL67452A (en) | 1985-12-31 |
| IL67452A0 (en) | 1983-05-15 |
| IE54283B1 (en) | 1989-08-16 |
| JPS58110598A (ja) | 1983-07-01 |
| KR850000978B1 (ko) | 1985-07-05 |
| GB2111497A (en) | 1983-07-06 |
| EP0082003B1 (en) | 1986-01-08 |
| KR840002855A (ko) | 1984-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |