JP2004526804A - アベルメクチンオキシム誘導体およびプラジクアンテルを含む獣医学的組成物 - Google Patents
アベルメクチンオキシム誘導体およびプラジクアンテルを含む獣医学的組成物 Download PDFInfo
- Publication number
- JP2004526804A JP2004526804A JP2002591005A JP2002591005A JP2004526804A JP 2004526804 A JP2004526804 A JP 2004526804A JP 2002591005 A JP2002591005 A JP 2002591005A JP 2002591005 A JP2002591005 A JP 2002591005A JP 2004526804 A JP2004526804 A JP 2004526804A
- Authority
- JP
- Japan
- Prior art keywords
- praziquantel
- selamectin
- monosaccharide
- formulation
- avermectin
- 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.)
- Withdrawn
Links
- FSVJFNAIGNNGKK-UHFFFAOYSA-N 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCC1 FSVJFNAIGNNGKK-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 229960002957 praziquantel Drugs 0.000 title claims abstract description 84
- 239000005660 Abamectin Substances 0.000 title claims abstract description 31
- -1 avermectin oxime Chemical class 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 title claims description 48
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 claims abstract description 64
- 229960002245 selamectin Drugs 0.000 claims abstract description 61
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 claims abstract description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 87
- 238000009472 formulation Methods 0.000 claims description 40
- 241000282326 Felis catus Species 0.000 claims description 38
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 27
- 241001465754 Metazoa Species 0.000 claims description 24
- 241000242722 Cestoda Species 0.000 claims description 20
- 206010061217 Infestation Diseases 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 244000045947 parasite Species 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 241000002163 Mesapamea fractilinea Species 0.000 claims description 6
- 241001674048 Phthiraptera Species 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 230000000699 topical effect Effects 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 239000004544 spot-on Substances 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 1
- 150000002772 monosaccharides Chemical class 0.000 claims 1
- 230000002141 anti-parasite Effects 0.000 abstract description 3
- 239000003096 antiparasitic agent Substances 0.000 abstract description 3
- 238000011284 combination treatment Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 19
- 241000282472 Canis lupus familiaris Species 0.000 description 14
- 239000003826 tablet Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 7
- 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 description 6
- 208000026368 Cestode infections Diseases 0.000 description 4
- 241000282465 Canis Species 0.000 description 3
- 241000244156 Hydatigera taeniaeformis Species 0.000 description 3
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- 206010047700 Vomiting Diseases 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
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- 231100000313 clinical toxicology Toxicity 0.000 description 3
- 238000002648 combination therapy Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 241000935794 Dipylidium Species 0.000 description 2
- 241001660203 Gasterophilus Species 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 244000078703 ectoparasite Species 0.000 description 2
- 244000079386 endoparasite Species 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229940102223 injectable solution Drugs 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
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- 241000894007 species Species 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 1
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 1
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 1
- 241000244203 Caenorhabditis elegans Species 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000935792 Dipylidium caninum Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000011887 Necropsy Methods 0.000 description 1
- 241000244187 Parascaris Species 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- 241001126263 Strongylidae Species 0.000 description 1
- 241000244155 Taenia Species 0.000 description 1
- 241001672170 Taenia pisiformis Species 0.000 description 1
- 229950008167 abamectin Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000002598 avermectinlike Effects 0.000 description 1
- 229940100037 biltricide Drugs 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 230000009193 crawling Effects 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- QLFZZSKTJWDQOS-YDBLARSUSA-N doramectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C3CCCCC3)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C QLFZZSKTJWDQOS-YDBLARSUSA-N 0.000 description 1
- 229960003997 doramectin Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940100036 droncit Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 230000008175 fetal development Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 229960002418 ivermectin Drugs 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 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 description 1
- YZBLFMPOMVTDJY-CBYMMZEQSA-N moxidectin Chemical compound O1[C@H](C(\C)=C\C(C)C)[C@@H](C)C(=N/OC)\C[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 YZBLFMPOMVTDJY-CBYMMZEQSA-N 0.000 description 1
- 229960004816 moxidectin Drugs 0.000 description 1
- PBYJDHRFPFHVKZ-UHFFFAOYSA-N n,n-dibutyl-4-hexoxynaphthalene-1-carboximidamide;hydrochloride Chemical compound Cl.C1=CC=C2C(OCCCCCC)=CC=C(C(=N)N(CCCC)CCCC)C2=C1 PBYJDHRFPFHVKZ-UHFFFAOYSA-N 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 229940096978 oral tablet Drugs 0.000 description 1
- 230000024241 parasitism Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 229940102101 selamectin topical solution Drugs 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0108485.4A GB0108485D0 (en) | 2001-04-04 | 2001-04-04 | Combination therapy |
| PCT/IB2002/001025 WO2002094288A1 (fr) | 2001-04-04 | 2002-03-28 | Compositions veterinaires comprenant des derives d'oxime avermectine et du praziquantel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2004526804A true JP2004526804A (ja) | 2004-09-02 |
Family
ID=9912257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002591005A Withdrawn JP2004526804A (ja) | 2001-04-04 | 2002-03-28 | アベルメクチンオキシム誘導体およびプラジクアンテルを含む獣医学的組成物 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1381374A1 (fr) |
| JP (1) | JP2004526804A (fr) |
| BR (1) | BR0208654A (fr) |
| CA (1) | CA2443068A1 (fr) |
| GB (1) | GB0108485D0 (fr) |
| MX (1) | MXPA03009023A (fr) |
| WO (1) | WO2002094288A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012053025A (ja) * | 2010-08-06 | 2012-03-15 | Maruishi Pharmaceutical Co Ltd | 含窒素複素環式化合物の定量方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1610613T3 (en) * | 2003-04-04 | 2017-02-27 | Merial Inc | TOPICAL ANTHELMINTIC VETERINARY FORMULATIONS |
| DE10358525A1 (de) | 2003-12-13 | 2005-07-07 | Bayer Healthcare Ag | Endoparasitizide Mittel zur topischen Applikation |
| FR2936710B1 (fr) * | 2008-10-07 | 2011-01-07 | Ceva Sante Animale | Composition veterinaire antiprolactinique destinee aux ruminants |
| EP2408771B1 (fr) | 2009-03-17 | 2016-11-16 | Concert Pharmaceuticals, Inc. | Composés de pyrazinoisoquinoline |
| GB0905365D0 (en) | 2009-03-27 | 2009-05-13 | Norbrook Lab Ltd | A topical parasiticide composition |
| UA108641C2 (uk) | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
| HUE041514T2 (hu) | 2012-02-06 | 2019-05-28 | Merial Inc | Szisztémásan ható hatóanyagokat tartalmazó, parazitaellenes, szájon át adagolt állatgyógyászati készítmények, eljárások és alkalmazásuk |
| JP6088637B2 (ja) | 2012-04-04 | 2017-03-01 | インターベット インターナショナル ベー． フェー． | イソオキサゾリン化合物のための固形経口医薬組成物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9300883D0 (en) * | 1993-01-18 | 1993-03-10 | Pfizer Ltd | Antiparasitic agents |
| BG61064B1 (bg) * | 1993-08-12 | 1996-10-31 | Илия Илиев | Лекарствено средство за обезпаразитяване на животни |
| AUPM969994A0 (en) * | 1994-11-28 | 1994-12-22 | Virbac S.A. | Equine anthelmintic formulations |
| WO1998006407A1 (fr) * | 1996-07-30 | 1998-02-19 | Ashmont Holdings Limited | Formulations anti-helminthes |
| GB9825402D0 (en) * | 1998-11-19 | 1999-01-13 | Pfizer Ltd | Antiparasitic formulations |
-
2001
- 2001-04-04 GB GBGB0108485.4A patent/GB0108485D0/en not_active Ceased
-
2002
- 2002-03-28 JP JP2002591005A patent/JP2004526804A/ja not_active Withdrawn
- 2002-03-28 BR BR0208654-9A patent/BR0208654A/pt not_active IP Right Cessation
- 2002-03-28 WO PCT/IB2002/001025 patent/WO2002094288A1/fr not_active Application Discontinuation
- 2002-03-28 MX MXPA03009023A patent/MXPA03009023A/es unknown
- 2002-03-28 CA CA002443068A patent/CA2443068A1/fr not_active Abandoned
- 2002-03-28 EP EP02716978A patent/EP1381374A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012053025A (ja) * | 2010-08-06 | 2012-03-15 | Maruishi Pharmaceutical Co Ltd | 含窒素複素環式化合物の定量方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2443068A1 (fr) | 2002-11-28 |
| MXPA03009023A (es) | 2004-02-12 |
| BR0208654A (pt) | 2004-03-09 |
| GB0108485D0 (en) | 2001-05-23 |
| WO2002094288A1 (fr) | 2002-11-28 |
| EP1381374A1 (fr) | 2004-01-21 |
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