ZA200502904B - Nodulisporic acid derivative spot-on formulations for combating parasites. - Google Patents
Nodulisporic acid derivative spot-on formulations for combating parasites. Download PDFInfo
- Publication number
- ZA200502904B ZA200502904B ZA200502904A ZA200502904A ZA200502904B ZA 200502904 B ZA200502904 B ZA 200502904B ZA 200502904 A ZA200502904 A ZA 200502904A ZA 200502904 A ZA200502904 A ZA 200502904A ZA 200502904 B ZA200502904 B ZA 200502904B
- Authority
- ZA
- South Africa
- Prior art keywords
- optionally substituted
- alkyl
- independently selected
- aryl
- groups independently
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 84
- 238000009472 formulation Methods 0.000 title claims description 66
- 239000004544 spot-on Substances 0.000 title claims description 55
- 244000045947 parasite Species 0.000 title claims description 49
- UNCVXXVJJXJZII-QLETUHIQSA-N 1k1cu6363a Chemical class OC(=O)C(/C)=C/C=C/[C@@](C)([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@]1(C)[C@@H]2CC2=C1N1[C@@H](C(=C)C)C(=O)C3=C([C@@H](O)[C@@H]4C(OC(C)(C)C=C44)(C)C)C4=CC2=C31 UNCVXXVJJXJZII-QLETUHIQSA-N 0.000 title claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 60
- -1 ) C(O)NR°RY Chemical group 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 49
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 44
- 229910052760 oxygen Inorganic materials 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 36
- 241001465754 Metazoa Species 0.000 claims description 35
- 241000124008 Mammalia Species 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000005842 heteroatom Chemical group 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
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- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 239000011593 sulfur Chemical group 0.000 claims description 22
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- 125000000304 alkynyl group Chemical group 0.000 claims description 20
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 15
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- 238000002955 isolation Methods 0.000 claims description 3
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- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 34
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- 125000003107 substituted aryl group Chemical group 0.000 claims 30
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims 7
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 2
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- YOWNVPAUWYHLQX-UHFFFAOYSA-N fluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 YOWNVPAUWYHLQX-UHFFFAOYSA-N 0.000 description 1
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- 239000005645 nematicide Substances 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- QZWHWHNCPFEXLL-UHFFFAOYSA-N propan-2-yl n-[2-(1,3-thiazol-4-yl)-3h-benzimidazol-5-yl]carbamate Chemical compound N1C2=CC(NC(=O)OC(C)C)=CC=C2N=C1C1=CSC=N1 QZWHWHNCPFEXLL-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A61K9/0017—Non-human animal skin, e.g. pour-on, spot-on
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Zoology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Epidemiology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
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US41562702P | 2002-10-02 | 2002-10-02 | |
US10/618,975 US20040077703A1 (en) | 2002-10-02 | 2003-07-14 | Nodulisporic acid derivative spot-on formulations for combating parasites |
PCT/US2003/030500 WO2004030457A1 (en) | 2002-10-02 | 2003-09-29 | Nodulisporic acid derivative spot-on formulations for combating parasites |
Publications (1)
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ZA200502904B true ZA200502904B (en) | 2005-10-19 |
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ZA200502904A ZA200502904B (en) | 2002-10-02 | 2005-04-11 | Nodulisporic acid derivative spot-on formulations for combating parasites. |
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US (1) | US20040077703A1 (es) |
EP (1) | EP1545211B1 (es) |
JP (1) | JP2006502241A (es) |
KR (2) | KR20070099668A (es) |
CN (1) | CN100496244C (es) |
AP (1) | AP2047A (es) |
AU (1) | AU2003279002A1 (es) |
BR (1) | BR0314531A (es) |
CA (1) | CA2500822C (es) |
CO (1) | CO5700750A2 (es) |
CR (2) | CR7810A (es) |
EA (1) | EA009683B1 (es) |
EC (1) | ECSP055736A (es) |
ES (1) | ES2482101T3 (es) |
GE (1) | GEP20084414B (es) |
HK (1) | HK1072348A1 (es) |
MA (1) | MA27457A1 (es) |
MX (1) | MXPA05003581A (es) |
NZ (1) | NZ539227A (es) |
UA (1) | UA83199C2 (es) |
WO (1) | WO2004030457A1 (es) |
ZA (1) | ZA200502904B (es) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US9416065B2 (en) * | 2007-02-12 | 2016-08-16 | Archer Daniels Midland Company | Adjuvants and methods of using them |
RU2497364C2 (ru) * | 2007-11-26 | 2013-11-10 | Мериал Лимитед | Системы растворителей для жидких наружных композиций для борьбы с паразитами |
EP2875726A1 (fr) | 2013-11-13 | 2015-05-27 | Ceva Animal Health | Nouvelles applications de compositions vétérinaires dans le traitement contre les parasites |
KR101687973B1 (ko) | 2015-12-08 | 2016-12-21 | 주식회사 씨티씨바이오 | 마이크로필름 코팅을 이용한 동물 사료용 프리믹스 제조방법 |
BR112020006214A2 (pt) * | 2017-09-29 | 2020-12-01 | Victoria Link Limited | biossíntese heteróloga de ácidos nodulispóricos |
KR102178885B1 (ko) * | 2020-01-17 | 2020-11-13 | 강현준 | 카프릴산을 포함하는 안정한 해충 방제제 및 이의 제조방법 |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3950360A (en) * | 1972-06-08 | 1976-04-13 | Sankyo Company Limited | Antibiotic substances |
SE434277B (sv) * | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
US4199569A (en) * | 1977-10-03 | 1980-04-22 | Merck & Co., Inc. | Selective hydrogenation products of C-076 compounds and derivatives thereof |
JPS57139012A (en) * | 1981-02-23 | 1982-08-27 | Sankyo Co Ltd | Anthelmintic composition |
US4427663A (en) * | 1982-03-16 | 1984-01-24 | Merck & Co., Inc. | 4"-Keto-and 4"-amino-4"-deoxy avermectin compounds and substituted amino derivatives thereof |
EP0237482A1 (de) * | 1986-03-06 | 1987-09-16 | Ciba-Geigy Ag | C(29)-Carbonyloxi-milbemycin-Derivate zur Bekämpfung von tier- und pflanzenparasitären Schädlingen |
AR243191A1 (es) * | 1986-03-25 | 1993-07-30 | Sankyo Co | Procedimiento para preparar compuestos de macrolida |
GB8613914D0 (en) * | 1986-06-07 | 1986-07-09 | Coopers Animal Health | Liquid formulations |
ATE75745T1 (de) * | 1986-07-02 | 1992-05-15 | Ciba Geigy Ag | Pestizide. |
US4855317A (en) * | 1987-03-06 | 1989-08-08 | Ciba-Geigy Corporation | Insecticides and parasiticides |
US4871719A (en) * | 1987-03-24 | 1989-10-03 | Ciba-Geigy Corporation | Composition for controlling parasites in productive livestock |
DE3888936T2 (de) * | 1987-11-03 | 1994-07-21 | Beecham Group Plc | Zwischenprodukte für die Herstellung makrolider Antibiotika mit anthelmintischer Wirkung. |
NZ232422A (en) * | 1989-02-16 | 1992-11-25 | Merck & Co Inc | 13-ketal milbemycin derivatives and parasiticides |
CA2036147A1 (en) * | 1990-06-29 | 1991-12-30 | Hiroki Tomioka | A 1-pyridylimidazole derivative and its production and use |
GB9205007D0 (en) * | 1992-03-07 | 1992-04-22 | Pfizer Ltd | Antiparasitic agents |
GB9300883D0 (en) | 1993-01-18 | 1993-03-10 | Pfizer Ltd | Antiparasitic agents |
DK0611774T3 (da) * | 1993-02-19 | 1999-11-15 | Hoffmann La Roche | Racemiseringsfri fremstilling af amider og peptider i nærværelse af katalytiske mængder af en N-hydroxyforbindelse |
GB9315108D0 (en) * | 1993-07-21 | 1993-09-01 | Pfizer Ltd | Antiparasitic agents |
US5399582A (en) * | 1993-11-01 | 1995-03-21 | Merck & Co., Inc. | Antiparasitic agents |
GB9402916D0 (en) * | 1994-02-16 | 1994-04-06 | Pfizer Ltd | Antiparasitic agents |
JPH0827018A (ja) * | 1994-07-22 | 1996-01-30 | Sanwa Kagaku Kenkyusho Co Ltd | 生理活性ペプチド又は蛋白質を含有する薬剤組成物 |
AUPM969994A0 (en) * | 1994-11-28 | 1994-12-22 | Virbac S.A. | Equine anthelmintic formulations |
US5595998A (en) * | 1994-12-15 | 1997-01-21 | Wolin; Ronald L. | Pyrazoloquinolines |
US6221894B1 (en) * | 1995-03-20 | 2001-04-24 | Merck & Co., Inc. | Nodulisporic acid derivatives |
EA003579B1 (ru) * | 1995-03-20 | 2003-06-26 | Мерк Энд Ко., Инк. | Производные нодулиспоровой кислоты |
US5595991A (en) * | 1995-03-20 | 1997-01-21 | Merck & Co., Inc. | Anthelmintic use of nodulisporic acid and analogs thereof |
US5962499A (en) * | 1995-03-20 | 1999-10-05 | Merck & Co., Inc. | Nodulisporic acid derivatives |
FR2739255B1 (fr) * | 1995-09-29 | 1998-09-04 | Rhone Merieux | Composition antiparasitaire pour le traitement et la protection des animaux de compagnie |
US5885607A (en) * | 1996-03-29 | 1999-03-23 | Rhone Merieux | N-phenylpyrazole-based anti-flea and anti-tick external device for cats and dogs |
IE80657B1 (en) * | 1996-03-29 | 1998-11-04 | Merial Sas | Insecticidal combination to control mammal fleas in particular fleas on cats and dogs |
US6010710A (en) * | 1996-03-29 | 2000-01-04 | Merial | Direct pour-on skin solution for antiparasitic use in cattle and sheep |
US5834260A (en) * | 1996-08-30 | 1998-11-10 | Merck & Co., Inc. | Antiparasitic agents |
FR2753377B1 (fr) * | 1996-09-19 | 1999-09-24 | Rhone Merieux | Nouvelle association parasiticide a base de 1-n-phenylpyra- zoles et de lactones macrocycliques endectocides |
DK0931082T3 (da) * | 1996-09-19 | 2003-04-22 | Merck & Co Inc | Nodulisporinsyrederivater |
US6426333B1 (en) * | 1996-09-19 | 2002-07-30 | Merial | Spot-on formulations for combating parasites |
US6136838A (en) * | 1998-03-19 | 2000-10-24 | Merck & Co., Inc. | Sulfurpentafluorophenylpyrazoles for controlling ectoparasitic infestations |
US6316644B1 (en) * | 1998-03-30 | 2001-11-13 | Lg Chemical Ltd. | Pilyethoxylated retinamide derivatives and process for preparing the same |
US6399796B2 (en) * | 2000-03-17 | 2002-06-04 | Roche Vitamins Inc. | Activation of a Diels-Alder reaction of a sterol 5,7-diene |
US6399786B1 (en) * | 2000-07-14 | 2002-06-04 | Merck & Co., Inc. | Nonacyclic nodulisporic acid derivatives |
US20040037869A1 (en) * | 2002-08-16 | 2004-02-26 | Douglas Cleverly | Non-animal product containing veterinary formulations |
US20050234119A1 (en) * | 2004-04-16 | 2005-10-20 | Soll Mark D | Antiparasitical agents and methods for treating, preventing and controlling external parasites in animals |
US20080003282A1 (en) * | 2005-04-18 | 2008-01-03 | Soll Mark D | Antiparasitical agents and methods for treating, preventing and controlling external parasites in animals |
-
2003
- 2003-07-14 US US10/618,975 patent/US20040077703A1/en not_active Abandoned
- 2003-09-29 KR KR1020077019588A patent/KR20070099668A/ko not_active Application Discontinuation
- 2003-09-29 ES ES03770513.4T patent/ES2482101T3/es not_active Expired - Lifetime
- 2003-09-29 AU AU2003279002A patent/AU2003279002A1/en not_active Abandoned
- 2003-09-29 BR BR0314531-0A patent/BR0314531A/pt not_active Application Discontinuation
- 2003-09-29 NZ NZ539227A patent/NZ539227A/en not_active IP Right Cessation
- 2003-09-29 KR KR1020057005819A patent/KR20050059235A/ko active Search and Examination
- 2003-09-29 WO PCT/US2003/030500 patent/WO2004030457A1/en active Application Filing
- 2003-09-29 GE GEAP20038771A patent/GEP20084414B/en unknown
- 2003-09-29 MX MXPA05003581A patent/MXPA05003581A/es unknown
- 2003-09-29 AP AP2005003289A patent/AP2047A/xx active
- 2003-09-29 CA CA2500822A patent/CA2500822C/en not_active Expired - Lifetime
- 2003-09-29 UA UAA200504055A patent/UA83199C2/ru unknown
- 2003-09-29 EP EP03770513.4A patent/EP1545211B1/en not_active Expired - Lifetime
- 2003-09-29 EA EA200500579A patent/EA009683B1/ru not_active IP Right Cessation
- 2003-09-29 JP JP2005500323A patent/JP2006502241A/ja active Pending
- 2003-09-29 CN CNB038253070A patent/CN100496244C/zh not_active Expired - Fee Related
-
2005
- 2005-04-11 ZA ZA200502904A patent/ZA200502904B/en unknown
- 2005-04-18 EC EC2005005736A patent/ECSP055736A/es unknown
- 2005-04-25 MA MA28236A patent/MA27457A1/fr unknown
- 2005-04-28 CR CR7810A patent/CR7810A/es unknown
- 2005-04-28 CO CO05040666A patent/CO5700750A2/es not_active Application Discontinuation
- 2005-07-08 HK HK05105754.0A patent/HK1072348A1/xx not_active IP Right Cessation
-
2008
- 2008-09-25 CR CR10319A patent/CR10319A/es unknown
Also Published As
Publication number | Publication date |
---|---|
AU2003279002A1 (en) | 2004-04-23 |
EP1545211B1 (en) | 2014-04-30 |
CN1700859A (zh) | 2005-11-23 |
BR0314531A (pt) | 2005-08-09 |
EA200500579A1 (ru) | 2005-08-25 |
KR20070099668A (ko) | 2007-10-09 |
HK1072348A1 (en) | 2005-08-26 |
AP2005003289A0 (en) | 2005-06-30 |
ES2482101T3 (es) | 2014-08-01 |
GEP20084414B (en) | 2008-07-10 |
WO2004030457A1 (en) | 2004-04-15 |
NZ539227A (en) | 2007-01-26 |
US20040077703A1 (en) | 2004-04-22 |
JP2006502241A (ja) | 2006-01-19 |
ECSP055736A (es) | 2005-09-20 |
KR20050059235A (ko) | 2005-06-17 |
UA83199C2 (ru) | 2008-06-25 |
CN100496244C (zh) | 2009-06-10 |
MA27457A1 (fr) | 2005-07-01 |
AP2047A (en) | 2009-09-18 |
EP1545211A1 (en) | 2005-06-29 |
CA2500822C (en) | 2013-12-24 |
MXPA05003581A (es) | 2005-06-17 |
CA2500822A1 (en) | 2004-04-15 |
CR7810A (es) | 2005-05-25 |
EA009683B1 (ru) | 2008-02-28 |
CR10319A (es) | 2008-10-21 |
CO5700750A2 (es) | 2006-11-30 |
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