CA2443068A1 - Compositions veterinaires comprenant des derives d'oxime avermectine et du praziquantel - Google Patents
Compositions veterinaires comprenant des derives d'oxime avermectine et du praziquantel Download PDFInfo
- Publication number
- CA2443068A1 CA2443068A1 CA002443068A CA2443068A CA2443068A1 CA 2443068 A1 CA2443068 A1 CA 2443068A1 CA 002443068 A CA002443068 A CA 002443068A CA 2443068 A CA2443068 A CA 2443068A CA 2443068 A1 CA2443068 A1 CA 2443068A1
- Authority
- CA
- Canada
- Prior art keywords
- praziquantel
- selamectin
- monosaccharide
- formulation
- treatment
- 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.)
- Abandoned
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 97
- 229960002957 praziquantel Drugs 0.000 title claims abstract description 92
- 239000000203 mixture Substances 0.000 title claims description 59
- 229960002245 selamectin Drugs 0.000 claims abstract description 68
- 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 67
- 239000005660 Abamectin Substances 0.000 claims abstract description 30
- 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 26
- -1 selamectin Chemical compound 0.000 claims abstract description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 46
- 238000009472 formulation Methods 0.000 claims description 46
- 238000011282 treatment Methods 0.000 claims description 32
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 31
- 241001465754 Metazoa Species 0.000 claims description 26
- 241000242722 Cestoda Species 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 206010061217 Infestation Diseases 0.000 claims description 14
- 230000003071 parasitic effect Effects 0.000 claims description 11
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 241000002163 Mesapamea fractilinea Species 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 238000011321 prophylaxis Methods 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 238000002648 combination therapy Methods 0.000 abstract description 4
- 230000002141 anti-parasite Effects 0.000 abstract description 3
- 239000003096 antiparasitic agent Substances 0.000 abstract description 3
- 241000282326 Felis catus Species 0.000 description 40
- 239000000243 solution Substances 0.000 description 21
- 241000282472 Canis lupus familiaris Species 0.000 description 16
- 239000003826 tablet Substances 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 13
- 208000015181 infectious disease Diseases 0.000 description 8
- 208000026368 Cestode infections Diseases 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 241000935794 Dipylidium Species 0.000 description 4
- 241000244156 Hydatigera taeniaeformis Species 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 244000045947 parasite Species 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- 239000007916 tablet composition Substances 0.000 description 4
- 241000935792 Dipylidium caninum Species 0.000 description 3
- 206010047700 Vomiting Diseases 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 231100000313 clinical toxicology Toxicity 0.000 description 3
- 230000035935 pregnancy Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 241000244206 Nematoda 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
- 241000244155 Taenia Species 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 244000078703 ectoparasite Species 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 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 2
- 230000007170 pathology Effects 0.000 description 2
- 229940075304 praziquantel injectable solution Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940102101 selamectin topical solution Drugs 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 1
- 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
- 241001626718 Anoplocephala Species 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241001660203 Gasterophilus Species 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
- 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 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
- 229940079593 drug Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000000408 embryogenic effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 230000008175 fetal development Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011835 investigation Methods 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
- 238000011068 loading method Methods 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
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[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 ZLBGSRMUSVULIE-GSMJGMFJSA-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
- 239000002674 ointment Substances 0.000 description 1
- 229940023486 oral product Drugs 0.000 description 1
- 239000013588 oral product Substances 0.000 description 1
- 229940096978 oral tablet Drugs 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000001556 precipitation Methods 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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)
Abstract
La présente invention concerne une polythérapie antiparasitaire faisant appel à une combinaison d'un 5-oxime avermectine monosaccharide 13, tel que de la sélamectine, et du praziquantel.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0108485.4 | 2001-04-04 | ||
| 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 |
|---|---|
| CA2443068A1 true CA2443068A1 (fr) | 2002-11-28 |
Family
ID=9912257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002443068A Abandoned CA2443068A1 (fr) | 2001-04-04 | 2002-03-28 | Compositions veterinaires comprenant des derives d'oxime avermectine et du praziquantel |
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) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05010659A (es) * | 2003-04-04 | 2005-12-12 | Merial Ltd | Formulaciones veterinarias antihelminticas topicas. |
| 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 |
| US8563554B2 (en) | 2009-03-17 | 2013-10-22 | Concert Pharmaceuticals, Inc. | Deuterated pyrazinoisoquinoline compounds |
| 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 | |
| JP5723567B2 (ja) * | 2010-08-06 | 2015-05-27 | 丸石製薬株式会社 | 含窒素複素環式化合物の定量方法 |
| DE112013000869T5 (de) | 2012-02-06 | 2014-10-16 | Merial Ltd. | Orale parasitizide Veterinärzusammensetzungen umfassend systemisch wirkende Wirkstoffe, Verfahren und Verwendun davon |
| RU2765231C2 (ru) | 2012-04-04 | 2022-01-26 | Интервет Интернэшнл Б.В. | Мягкие жевательные фармацевтические продукты |
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 |
| CA2260143C (fr) * | 1996-07-30 | 2004-07-13 | 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 BR BR0208654-9A patent/BR0208654A/pt not_active IP Right Cessation
- 2002-03-28 CA CA002443068A patent/CA2443068A1/fr not_active Abandoned
- 2002-03-28 MX MXPA03009023A patent/MXPA03009023A/es unknown
- 2002-03-28 JP JP2002591005A patent/JP2004526804A/ja not_active Withdrawn
- 2002-03-28 EP EP02716978A patent/EP1381374A1/fr not_active Withdrawn
- 2002-03-28 WO PCT/IB2002/001025 patent/WO2002094288A1/fr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004526804A (ja) | 2004-09-02 |
| BR0208654A (pt) | 2004-03-09 |
| WO2002094288A1 (fr) | 2002-11-28 |
| MXPA03009023A (es) | 2004-02-12 |
| EP1381374A1 (fr) | 2004-01-21 |
| GB0108485D0 (en) | 2001-05-23 |
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