NO323751B1 - 13-substituerte milbemycinderivater, preparater omfattende disse og anvendelse av dem mot insekter og andre skadedyr - Google Patents
13-substituerte milbemycinderivater, preparater omfattende disse og anvendelse av dem mot insekter og andre skadedyr Download PDFInfo
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- NO323751B1 NO323751B1 NO20025141A NO20025141A NO323751B1 NO 323751 B1 NO323751 B1 NO 323751B1 NO 20025141 A NO20025141 A NO 20025141A NO 20025141 A NO20025141 A NO 20025141A NO 323751 B1 NO323751 B1 NO 323751B1
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- 241000238631 Hexapoda Species 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 6
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 title description 27
- 241000607479 Yersinia pestis Species 0.000 title description 7
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- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 161
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- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 49
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 17
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- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229930027917 kanamycin Natural products 0.000 description 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
- 229960000318 kanamycin Drugs 0.000 description 1
- 229930182823 kanamycin A Natural products 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- UQPSGBZICXWIAG-UHFFFAOYSA-L nickel(2+);dibromide;trihydrate Chemical compound O.O.O.Br[Ni]Br UQPSGBZICXWIAG-UHFFFAOYSA-L 0.000 description 1
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- MLBYLEUJXUBIJJ-UHFFFAOYSA-N pent-4-ynoic acid Chemical compound OC(=O)CCC#C MLBYLEUJXUBIJJ-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([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
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000127209 | 2000-04-27 | ||
| PCT/JP2001/003656 WO2001083500A1 (en) | 2000-04-27 | 2001-04-26 | 13-substituted milbemycin derivatives, their preparation and their use against insects and other pests |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20025141D0 NO20025141D0 (no) | 2002-10-25 |
| NO20025141L NO20025141L (no) | 2002-12-16 |
| NO323751B1 true NO323751B1 (no) | 2007-07-02 |
Family
ID=18636847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20025141A NO323751B1 (no) | 2000-04-27 | 2002-10-25 | 13-substituerte milbemycinderivater, preparater omfattende disse og anvendelse av dem mot insekter og andre skadedyr |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6653342B2 (ko) |
| EP (1) | EP1276748B1 (ko) |
| KR (1) | KR100711931B1 (ko) |
| CN (1) | CN1247607C (ko) |
| AR (1) | AR029250A1 (ko) |
| AT (1) | ATE315573T1 (ko) |
| AU (2) | AU5261301A (ko) |
| BR (1) | BR0110385A (ko) |
| CA (1) | CA2407611A1 (ko) |
| CZ (1) | CZ20023565A3 (ko) |
| DE (1) | DE60116615T2 (ko) |
| DK (1) | DK1276748T3 (ko) |
| ES (1) | ES2254400T3 (ko) |
| HK (1) | HK1057757A1 (ko) |
| HU (1) | HUP0301040A3 (ko) |
| IL (1) | IL152449A0 (ko) |
| MX (1) | MXPA02010587A (ko) |
| NO (1) | NO323751B1 (ko) |
| NZ (1) | NZ522247A (ko) |
| PL (1) | PL357598A1 (ko) |
| RU (1) | RU2226531C1 (ko) |
| TW (1) | TWI285206B (ko) |
| WO (1) | WO2001083500A1 (ko) |
| ZA (1) | ZA200208630B (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL370227A1 (en) * | 2001-10-25 | 2005-05-16 | Sankyo Lifetech Company, Limited | Anthelmintic composition |
| TWI366442B (en) | 2003-07-30 | 2012-06-21 | Novartis Ag | Palatable ductile chewable veterinary composition |
| US20090281175A1 (en) * | 2006-09-28 | 2009-11-12 | Galderma S.A. | Avermectin compounds and treatment of dermatological disorders in humans therewith |
| US8426460B2 (en) | 2008-12-04 | 2013-04-23 | Merial Limited | Dimeric avermectin and milbemycin derivatives |
| US8980896B2 (en) | 2009-12-17 | 2015-03-17 | Merial, Inc. | Compositions comprising macrocyclic lactone compounds and spirodioxepinoindoles |
| DK3351546T5 (da) | 2011-12-02 | 2024-08-12 | Boehringer Ingelheim Vetmedica Gmbh | Langtidsvirkende injicerbare moxidectinformuleringer |
| PE20151726A1 (es) | 2013-04-12 | 2015-11-18 | Zoetis Services Llc | Formulaciones veterinarias estables de combinacion de lactonas macrociclicas e imidazotiazoles |
| JP2022520152A (ja) * | 2018-12-21 | 2022-03-29 | エランコ・ユーエス・インコーポレイテッド | 殺寄生生物製剤およびその使用 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206205A (en) | 1977-10-03 | 1980-06-03 | Merck & Co., Inc. | Monosaccharide and aglycone derivatives of C-076 |
| NZ188459A (en) | 1977-10-03 | 1982-09-07 | Merck & Co Inc | Derivatives of c-076 compounds and pesticidal compositions |
| US4201861A (en) | 1977-10-03 | 1980-05-06 | Merck & Co., Inc. | Acyl derivatives of C-076 compounds |
| US4171314A (en) | 1977-12-19 | 1979-10-16 | Merck & Co., Inc. | 13-Halo and 13-deoxy C-076 compounds |
| US4173571A (en) | 1977-12-19 | 1979-11-06 | Merck & Co., Inc. | 13-Halo and 13-deoxy derivatives of C-076 compounds |
| US4203976A (en) | 1978-08-02 | 1980-05-20 | Merck & Co., Inc. | Sugar derivatives of C-076 compounds |
| US4200581A (en) | 1978-08-04 | 1980-04-29 | Merck & Co., Inc. | Alkyl derivatives of C-076 compounds |
| US4289760A (en) | 1980-05-02 | 1981-09-15 | Merck & Co., Inc. | 23-Keto derivatives of C-076 compounds |
| JPS57120589A (en) | 1981-01-20 | 1982-07-27 | Sankyo Co Ltd | 5-methoxy and 5-lower alkanoyloxy derivative, its preparation and acaricide and parasiticide |
| IT1144368B (it) | 1981-05-20 | 1986-10-29 | Gaudino Di P Gaudino & C Sas O | Perfezionamenti nei laminatoi con almeno un campo di stiro per la filatura diretta di pettinato e semipettinato |
| US4457920A (en) | 1981-09-03 | 1984-07-03 | Merck & Co., Inc. | 4a-Substituted avermectin compounds |
| US4423209A (en) | 1982-02-26 | 1983-12-27 | Merck & Co., Inc. | Processes for the interconversion of avermectin compounds |
| JPS5916894A (ja) | 1982-07-21 | 1984-01-28 | Sankyo Co Ltd | ミルベマイシンｄの５−アシルオキシ誘導体 |
| JPS5920285A (ja) | 1982-07-23 | 1984-02-01 | Sankyo Co Ltd | ミルベマイシンｄの５−二塩基酸エステル誘導体及びその塩 |
| 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 |
| US4469682A (en) | 1983-01-28 | 1984-09-04 | Merck & Co., Inc. | Avermectin and milbemycin phosphate esters, pharmaceutical compositions, and method of use |
| 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 |
| EP0180539A1 (de) | 1984-09-18 | 1986-05-07 | Ciba-Geigy Ag | 13-Halo- und 13-Hydroximilbemycine |
| US4696922A (en) | 1984-11-26 | 1987-09-29 | Ciba-Geigy Corporation | 5-azolylacetoxymilbemycins as ecto- and endoparasites |
| JPS6289685A (ja) | 1985-05-31 | 1987-04-24 | Sankyo Co Ltd | １３−ハロゲンミルベマイシン誘導体 |
| DE3767560D1 (de) | 1986-03-25 | 1991-02-28 | Sankyo Co | Makrolide verbindungen, ihre herstellung und verwendung. |
| US5614470A (en) * | 1994-04-01 | 1997-03-25 | Sankyo Company, Limited | 13-substituted milbemycin derivatives, their preparation and their use |
| NZ299460A (en) | 1995-09-29 | 1997-12-19 | Sankyo Co | 13-substituted milbemycin 5-oxime derivatives; veterinary pesticides |
-
2001
- 2001-04-26 CA CA002407611A patent/CA2407611A1/en not_active Abandoned
- 2001-04-26 BR BR0110385-7A patent/BR0110385A/pt not_active IP Right Cessation
- 2001-04-26 TW TW090109990A patent/TWI285206B/zh not_active IP Right Cessation
- 2001-04-26 AU AU5261301A patent/AU5261301A/xx active Pending
- 2001-04-26 KR KR1020027013834A patent/KR100711931B1/ko not_active IP Right Cessation
- 2001-04-26 AU AU2001252613A patent/AU2001252613B2/en not_active Ceased
- 2001-04-26 RU RU2002131794/04A patent/RU2226531C1/ru not_active IP Right Cessation
- 2001-04-26 DE DE60116615T patent/DE60116615T2/de not_active Expired - Fee Related
- 2001-04-26 AT AT01925985T patent/ATE315573T1/de not_active IP Right Cessation
- 2001-04-26 DK DK01925985T patent/DK1276748T3/da active
- 2001-04-26 HU HU0301040A patent/HUP0301040A3/hu unknown
- 2001-04-26 CZ CZ20023565A patent/CZ20023565A3/cs unknown
- 2001-04-26 ES ES01925985T patent/ES2254400T3/es not_active Expired - Lifetime
- 2001-04-26 CN CNB018119832A patent/CN1247607C/zh not_active Expired - Fee Related
- 2001-04-26 MX MXPA02010587A patent/MXPA02010587A/es active IP Right Grant
- 2001-04-26 WO PCT/JP2001/003656 patent/WO2001083500A1/en active IP Right Grant
- 2001-04-26 PL PL01357598A patent/PL357598A1/xx unknown
- 2001-04-26 IL IL15244901A patent/IL152449A0/xx unknown
- 2001-04-26 NZ NZ522247A patent/NZ522247A/en unknown
- 2001-04-26 EP EP01925985A patent/EP1276748B1/en not_active Expired - Lifetime
- 2001-04-27 AR ARP010102004A patent/AR029250A1/es not_active Application Discontinuation
-
2002
- 2002-10-22 US US10/277,993 patent/US6653342B2/en not_active Expired - Fee Related
- 2002-10-24 ZA ZA200208630A patent/ZA200208630B/en unknown
- 2002-10-25 NO NO20025141A patent/NO323751B1/no not_active IP Right Cessation
-
2004
- 2004-01-21 HK HK04100487A patent/HK1057757A1/xx not_active IP Right Cessation
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