HU201765B - Process for producing 23-oxo and 23-imino derivatives of mono- and diepoxides of ll-f28249 compounds and pharmaceutical compositions comprising such compounds as active ingredient - Google Patents
Process for producing 23-oxo and 23-imino derivatives of mono- and diepoxides of ll-f28249 compounds and pharmaceutical compositions comprising such compounds as active ingredient Download PDFInfo
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- HU201765B HU201765B HU881071A HU107188A HU201765B HU 201765 B HU201765 B HU 201765B HU 881071 A HU881071 A HU 881071A HU 107188 A HU107188 A HU 107188A HU 201765 B HU201765 B HU 201765B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 79
- 239000004480 active ingredient Substances 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims description 23
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- 238000011282 treatment Methods 0.000 claims abstract description 15
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- 206010061217 Infestation Diseases 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
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- 238000006243 chemical reaction Methods 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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- 238000012512 characterization method Methods 0.000 description 1
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- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000000515 cyanogenic effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 208000035474 group of disease Diseases 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/022,850 US4886829A (en) | 1987-03-06 | 1987-03-06 | 23-Oxo (keto) and 23-imino derivatives of mono- and diepoxy LL-F28249 compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT46013A HUT46013A (en) | 1988-09-28 |
| HU201765B true HU201765B (en) | 1990-12-28 |
Family
ID=21811757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU881071A HU201765B (en) | 1987-03-06 | 1988-03-04 | Process for producing 23-oxo and 23-imino derivatives of mono- and diepoxides of ll-f28249 compounds and pharmaceutical compositions comprising such compounds as active ingredient |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4886829A (en, 2012) |
| EP (1) | EP0293549B1 (en, 2012) |
| JP (1) | JP2583946B2 (en, 2012) |
| KR (1) | KR960007867B1 (en, 2012) |
| AR (1) | AR246525A1 (en, 2012) |
| AT (1) | ATE96802T1 (en, 2012) |
| AU (1) | AU600561B2 (en, 2012) |
| BR (1) | BR8800944A (en, 2012) |
| CA (1) | CA1301165C (en, 2012) |
| DE (1) | DE3885346T2 (en, 2012) |
| DK (1) | DK167189B1 (en, 2012) |
| ES (1) | ES2059410T3 (en, 2012) |
| GR (1) | GR3009687T3 (en, 2012) |
| HU (1) | HU201765B (en, 2012) |
| IE (1) | IE62520B1 (en, 2012) |
| IL (1) | IL85391A0 (en, 2012) |
| NZ (1) | NZ223642A (en, 2012) |
| PT (1) | PT86898B (en, 2012) |
| ZA (1) | ZA881581B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4851428A (en) * | 1987-03-06 | 1989-07-25 | American Cyanamid Company | Mono- and diepoxide derivatives of Δ22-LL-F28249 compounds |
| US4857544A (en) * | 1987-03-06 | 1989-08-15 | American Cyanamid Company | 27-Halo derivatives of LL-F28249 compounds |
| US4876272A (en) * | 1987-03-06 | 1989-10-24 | American Cyanamid Company | Mono- and diepoxide derivatives of LL-F28249 compounds |
| US5322692A (en) * | 1989-02-28 | 1994-06-21 | American Cyanamid Company | Sustained release bolus effective for the prolonged prevention, treatment or control of nematode, acarid and endo- and ectoparasitic infestations of ruminants |
| DK0385106T3 (da) * | 1989-02-28 | 1994-04-11 | American Cyanamid Co | Bolus med forhalet frigivelse effektiv til forlænget prævention eller behandling af eller kontrol med nematode-, mide- og endo- og ektoparasitiske infektioner hos drøvtyggere |
| ATE130006T1 (de) * | 1989-09-11 | 1995-11-15 | American Cyanamid Co | 13-alkyl-23-imino und 13-halo-23-imino-derivate von ll-f28249-verbindungen und ihre verwendung als endo- und ectoparasitizide, insektizide, akarizide und nematozide mittel. |
| CA2105251C (en) * | 1992-09-01 | 2004-12-07 | Mitsugi Shibano | Novel processes for the production of 13-ether derivatives of milbemycins, and novel intermediates therefor |
| GB9402916D0 (en) * | 1994-02-16 | 1994-04-06 | Pfizer Ltd | Antiparasitic agents |
| WO1999017760A2 (en) | 1997-10-02 | 1999-04-15 | Microcide Pharmaceuticals, Inc. | Fungal or mammalian cell efflux pump inhibitors for enhancing susceptibility of the cell to a drug |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201861A (en) * | 1977-10-03 | 1980-05-06 | Merck & Co., Inc. | Acyl derivatives of C-076 compounds |
| US4289760A (en) * | 1980-05-02 | 1981-09-15 | Merck & Co., Inc. | 23-Keto derivatives of C-076 compounds |
| US4423209A (en) * | 1982-02-26 | 1983-12-27 | Merck & Co., Inc. | Processes for the interconversion of avermectin compounds |
| JPS59108785A (ja) * | 1982-11-25 | 1984-06-23 | Sankyo Co Ltd | ミルベマイシン類の５−オキシム誘導体 |
| US4530921A (en) * | 1983-10-03 | 1985-07-23 | Merck & Co., Inc. | Avermectin epoxide derivatives and method of use |
| DK165119C (da) * | 1984-06-05 | 1993-03-01 | American Cyanamid Co | Antibiotiske forbindelser betegnet ll-f28249alfa, beta, gamma, delta, epsilon, zeta, eta, theta, iota, kappa, my og ny og pharmaceutisk or pharmakologisk acceptable salte deraf samt fremgangsmaade til deres fremstilling |
| US4579864A (en) * | 1984-06-11 | 1986-04-01 | Merck & Co., Inc. | Avermectin and milbemycin 13-keto, 13-imino and 13-amino derivatives |
| US4547491A (en) * | 1984-07-18 | 1985-10-15 | Merck & Co., Inc. | C-8A-Oxo-avermectin and milbemycin derivatives, pharmaceutical compositions and method of use |
| IT1182857B (it) * | 1984-09-14 | 1987-10-05 | Glaxo Group Ltd | Composti antibiotici, composizioni antiparassitarie che li contengono e procedimento per prepararli ed applicarli |
| US4696922A (en) * | 1984-11-26 | 1987-09-29 | Ciba-Geigy Corporation | 5-azolylacetoxymilbemycins as ecto- and endoparasites |
| AU596586B2 (en) * | 1985-04-30 | 1990-05-10 | American Cyanamid Company | Chemical derivatives of antibiotics S541 |
| AU598204B2 (en) * | 1985-09-13 | 1990-06-21 | American Cyanamid Company | Chemical derivatives of antibiotics S541 |
| GB8606108D0 (en) * | 1986-03-12 | 1986-04-16 | Glaxo Group Ltd | Chemical compounds |
| DE3787548T2 (de) * | 1986-03-12 | 1994-03-31 | American Cyanamid Co | Makrolid-Verbindungen. |
| US4876272A (en) * | 1987-03-06 | 1989-10-24 | American Cyanamid Company | Mono- and diepoxide derivatives of LL-F28249 compounds |
| US4857544A (en) * | 1987-03-06 | 1989-08-15 | American Cyanamid Company | 27-Halo derivatives of LL-F28249 compounds |
-
1987
- 1987-03-06 US US07/022,850 patent/US4886829A/en not_active Expired - Lifetime
-
1988
- 1988-02-05 AT AT88101684T patent/ATE96802T1/de not_active IP Right Cessation
- 1988-02-05 ES ES88101684T patent/ES2059410T3/es not_active Expired - Lifetime
- 1988-02-05 DE DE3885346T patent/DE3885346T2/de not_active Expired - Lifetime
- 1988-02-05 EP EP88101684A patent/EP0293549B1/en not_active Expired - Lifetime
- 1988-02-10 IL IL85391A patent/IL85391A0/xx not_active IP Right Cessation
- 1988-02-25 NZ NZ223642A patent/NZ223642A/xx unknown
- 1988-03-03 AR AR88310217A patent/AR246525A1/es active
- 1988-03-04 JP JP63049892A patent/JP2583946B2/ja not_active Expired - Lifetime
- 1988-03-04 HU HU881071A patent/HU201765B/hu unknown
- 1988-03-04 IE IE61888A patent/IE62520B1/en not_active IP Right Cessation
- 1988-03-04 AU AU12712/88A patent/AU600561B2/en not_active Expired
- 1988-03-04 CA CA000560571A patent/CA1301165C/en not_active Expired - Lifetime
- 1988-03-04 BR BR8800944A patent/BR8800944A/pt not_active IP Right Cessation
- 1988-03-04 KR KR1019880002275A patent/KR960007867B1/ko not_active Expired - Fee Related
- 1988-03-04 DK DK119688A patent/DK167189B1/da not_active IP Right Cessation
- 1988-03-04 PT PT86898A patent/PT86898B/pt not_active IP Right Cessation
- 1988-03-04 ZA ZA881581A patent/ZA881581B/xx unknown
-
1993
- 1993-11-10 GR GR930400611T patent/GR3009687T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR8800944A (pt) | 1988-10-11 |
| IE62520B1 (en) | 1995-02-08 |
| JPS63277681A (ja) | 1988-11-15 |
| KR960007867B1 (ko) | 1996-06-13 |
| IE880618L (en) | 1988-09-06 |
| EP0293549B1 (en) | 1993-11-03 |
| ATE96802T1 (de) | 1993-11-15 |
| PT86898B (pt) | 1992-05-29 |
| US4886829A (en) | 1989-12-12 |
| AU1271288A (en) | 1988-09-08 |
| IL85391A0 (en) | 1988-07-31 |
| AR246525A1 (es) | 1994-08-31 |
| HUT46013A (en) | 1988-09-28 |
| NZ223642A (en) | 1991-01-29 |
| DK119688D0 (da) | 1988-03-04 |
| ES2059410T3 (es) | 1994-11-16 |
| DK167189B1 (da) | 1993-09-13 |
| CA1301165C (en) | 1992-05-19 |
| ZA881581B (en) | 1988-08-29 |
| AU600561B2 (en) | 1990-08-16 |
| DE3885346T2 (de) | 1994-05-19 |
| DE3885346D1 (de) | 1993-12-09 |
| PT86898A (pt) | 1988-04-01 |
| EP0293549A1 (en) | 1988-12-07 |
| DK119688A (da) | 1988-09-07 |
| KR880011162A (ko) | 1988-10-26 |
| GR3009687T3 (en, 2012) | 1994-02-28 |
| JP2583946B2 (ja) | 1997-02-19 |
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