DE69327074T2 - Substituierte 1,2,4-Triazine-3,5-Dion Derivate und diese enthaltende Arzneimittel, insbesondere zur Behandlung von Coccidiose - Google Patents
Substituierte 1,2,4-Triazine-3,5-Dion Derivate und diese enthaltende Arzneimittel, insbesondere zur Behandlung von CoccidioseInfo
- Publication number
- DE69327074T2 DE69327074T2 DE69327074T DE69327074T DE69327074T2 DE 69327074 T2 DE69327074 T2 DE 69327074T2 DE 69327074 T DE69327074 T DE 69327074T DE 69327074 T DE69327074 T DE 69327074T DE 69327074 T2 DE69327074 T2 DE 69327074T2
- Authority
- DE
- Germany
- Prior art keywords
- pyridyl
- group
- pyrimidinyl
- trifluoromethyl
- methyl
- 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 - Fee Related
Links
- 239000003814 drug Chemical class 0.000 title claims description 20
- 208000003495 Coccidiosis Diseases 0.000 title claims description 14
- 206010023076 Isosporiasis Diseases 0.000 title claims description 14
- SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical class O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 title claims description 9
- -1 5-chloro-2-pyridyl Chemical group 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 56
- 244000144977 poultry Species 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003651 drinking water Substances 0.000 claims description 4
- 235000020188 drinking water Nutrition 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000001165 anti-coccidial effect Effects 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 229940079593 drug Drugs 0.000 description 11
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- 235000013594 poultry meat Nutrition 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 208000035861 hematochezia Diseases 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
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- 230000003902 lesion Effects 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 6
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 238000006467 substitution reaction Methods 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- NQTMZDVIRNUKPI-UHFFFAOYSA-N 1-n-(5-bromopyrimidin-2-yl)-2,6-dichlorobenzene-1,4-diamine Chemical compound ClC1=CC(N)=CC(Cl)=C1NC1=NC=C(Br)C=N1 NQTMZDVIRNUKPI-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- OVLASTGNOGMGMW-UHFFFAOYSA-N 2,6-dichloro-1-n-(5-chloropyridin-2-yl)benzene-1,4-diamine Chemical compound ClC1=CC(N)=CC(Cl)=C1NC1=CC=C(Cl)C=N1 OVLASTGNOGMGMW-UHFFFAOYSA-N 0.000 description 1
- SLZLRTNJKWFIFU-UHFFFAOYSA-N 2,6-dichloro-1-n-(5-chloropyrimidin-2-yl)benzene-1,4-diamine Chemical compound ClC1=CC(N)=CC(Cl)=C1NC1=NC=C(Cl)C=N1 SLZLRTNJKWFIFU-UHFFFAOYSA-N 0.000 description 1
- XPFNUDZGXBCDPJ-UHFFFAOYSA-N 2,6-dichloro-1-n-(5-methyl-1,2-oxazol-3-yl)benzene-1,4-diamine Chemical compound O1C(C)=CC(NC=2C(=CC(N)=CC=2Cl)Cl)=N1 XPFNUDZGXBCDPJ-UHFFFAOYSA-N 0.000 description 1
- OUUSIJKVGUEKOK-UHFFFAOYSA-N 2,6-dichloro-1-n-(5-methylpyridin-2-yl)benzene-1,4-diamine Chemical compound N1=CC(C)=CC=C1NC1=C(Cl)C=C(N)C=C1Cl OUUSIJKVGUEKOK-UHFFFAOYSA-N 0.000 description 1
- NIWGMSSUEGELDR-UHFFFAOYSA-N 2,6-dichloro-1-n-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]benzene-1,4-diamine Chemical compound ClC1=CC(N)=CC(Cl)=C1NC1=NC=C(C(F)(F)F)C=C1Cl NIWGMSSUEGELDR-UHFFFAOYSA-N 0.000 description 1
- FKNQJENKNVRMKE-UHFFFAOYSA-N 2,6-dichloro-1-n-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]benzene-1,4-diamine Chemical compound ClC1=CC(N)=CC(Cl)=C1NC1=NN=C(C(F)(F)F)S1 FKNQJENKNVRMKE-UHFFFAOYSA-N 0.000 description 1
- WPXMBJNSRMMQHE-UHFFFAOYSA-N 2,6-dichloro-1-n-pyridin-3-ylbenzene-1,4-diamine Chemical compound ClC1=CC(N)=CC(Cl)=C1NC1=CC=CN=C1 WPXMBJNSRMMQHE-UHFFFAOYSA-N 0.000 description 1
- MXKQCADOUYMMSK-UHFFFAOYSA-N 2,6-dichloro-1-n-pyrimidin-2-ylbenzene-1,4-diamine Chemical compound ClC1=CC(N)=CC(Cl)=C1NC1=NC=CC=N1 MXKQCADOUYMMSK-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZDPIZLCVJAAHHR-UHFFFAOYSA-N Clopidol Chemical compound CC1=NC(C)=C(Cl)C(O)=C1Cl ZDPIZLCVJAAHHR-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
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- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000011887 Necropsy Methods 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KQXDHUJYNAXLNZ-XQSDOZFQSA-N Salinomycin Chemical compound O1[C@@H]([C@@H](CC)C(O)=O)CC[C@H](C)[C@@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 KQXDHUJYNAXLNZ-XQSDOZFQSA-N 0.000 description 1
- 239000004189 Salinomycin Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- HSOGVWWWGVFXGF-UHFFFAOYSA-N ethyl n-(2-cyanoacetyl)carbamate Chemical compound CCOC(=O)NC(=O)CC#N HSOGVWWWGVFXGF-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16783792 | 1992-06-25 | ||
| JP13760593A JP3288132B2 (ja) | 1992-06-25 | 1993-06-08 | 置換１，２，４−トリアジン−３，５−ジオンおよびそれを有効成分とする抗コクシジウム組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69327074D1 DE69327074D1 (de) | 1999-12-30 |
| DE69327074T2 true DE69327074T2 (de) | 2000-03-16 |
Family
ID=26470855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69327074T Expired - Fee Related DE69327074T2 (de) | 1992-06-25 | 1993-06-22 | Substituierte 1,2,4-Triazine-3,5-Dion Derivate und diese enthaltende Arzneimittel, insbesondere zur Behandlung von Coccidiose |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5424310A (enExample) |
| EP (1) | EP0576251B1 (enExample) |
| JP (1) | JP3288132B2 (enExample) |
| KR (1) | KR100299396B1 (enExample) |
| AU (1) | AU658306B2 (enExample) |
| BR (1) | BR9302641A (enExample) |
| CA (1) | CA2098650A1 (enExample) |
| DE (1) | DE69327074T2 (enExample) |
| TW (1) | TW303366B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2707294B1 (fr) * | 1993-07-06 | 1995-09-29 | Pf Medicament | Nouveaux dérivés de la 3,5-dioxo-(2H,4H)-1,2,4-triazine, leur préparation et leur application en thérapeutique humaine. |
| US5747476A (en) | 1996-07-17 | 1998-05-05 | Mortar & Pestle Veterinary Pharmacy, Inc. | Treatment of equine protozoal myeloencephalitis |
| US7329288B2 (en) | 2004-02-27 | 2008-02-12 | L'oreal S.A. | N-heteroaryl secondary para-phenylenediamine, a dye composition comprising such a para-phenylenediamine, a process for preparing this composition and use thereof |
| FR2866887A1 (fr) * | 2004-02-27 | 2005-09-02 | Oreal | Para-phenylenediamine secondaire n-heteroaryle, compositon tinctoriale comprenant une telle para-phenylenediamine, procede mettant en oeuvre cette composition et utilisation |
| DE102009038949A1 (de) * | 2009-08-26 | 2011-03-03 | Bayer Animal Health Gmbh | Neue Verwendung von heterocyclisch substituierten 1,2,4-Triazindionen |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912723A (en) | 1971-03-29 | 1975-10-14 | Pfizer | 2-Phenyl-as-triazine-3,5(2H,4H)diones |
| GB1448696A (en) * | 1973-05-29 | 1976-09-08 | Pfizer | 2-phqnyl-astriazine-3,4-2h,4h-diones |
| DE2532363A1 (de) * | 1975-07-19 | 1977-02-03 | Bayer Ag | Substituierte 2-phenyl-1,2,4- triazin-3,5(2h,4h)-dione, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2606850A1 (de) * | 1976-02-20 | 1977-09-15 | Hoechst Ag | Substituierte p-aminophenyl-as- triazindione und ihre herstellung |
| DE3805660A1 (de) * | 1988-02-24 | 1989-09-07 | Bayer Ag | Substituierte 1,2,4-triazindione, verfahren zu ihrer herstellung und ihre verwendung |
| DE3814323A1 (de) * | 1988-04-28 | 1989-11-09 | Hoechst Ag | Wasserloesliche zubereitungen von coccidiostatica |
| US5214043A (en) * | 1989-01-09 | 1993-05-25 | Bayer Aktiengesellschaft | Parasiticidal substituted hexahydro-1,2,4-triazinediones |
| EP0377903A3 (de) * | 1989-01-09 | 1991-07-17 | Bayer Ag | Substituierte Hexahydro-1,2,4-triazindione, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung |
-
1993
- 1993-06-08 JP JP13760593A patent/JP3288132B2/ja not_active Expired - Fee Related
- 1993-06-17 CA CA002098650A patent/CA2098650A1/en not_active Abandoned
- 1993-06-18 AU AU41326/93A patent/AU658306B2/en not_active Ceased
- 1993-06-22 EP EP93304858A patent/EP0576251B1/en not_active Expired - Lifetime
- 1993-06-22 DE DE69327074T patent/DE69327074T2/de not_active Expired - Fee Related
- 1993-06-23 US US08/079,925 patent/US5424310A/en not_active Expired - Fee Related
- 1993-06-23 TW TW082105041A patent/TW303366B/zh active
- 1993-06-24 KR KR1019930011559A patent/KR100299396B1/ko not_active Expired - Fee Related
- 1993-06-24 BR BR9302641A patent/BR9302641A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR940005618A (ko) | 1994-03-21 |
| JPH0673048A (ja) | 1994-03-15 |
| US5424310A (en) | 1995-06-13 |
| EP0576251B1 (en) | 1999-11-24 |
| BR9302641A (pt) | 1994-02-16 |
| CA2098650A1 (en) | 1993-12-26 |
| TW303366B (enExample) | 1997-04-21 |
| JP3288132B2 (ja) | 2002-06-04 |
| DE69327074D1 (de) | 1999-12-30 |
| AU658306B2 (en) | 1995-04-06 |
| EP0576251A1 (en) | 1993-12-29 |
| AU4132693A (en) | 1994-01-06 |
| KR100299396B1 (ko) | 2001-11-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |