CA2703008A1 - Anthelmintic paste comprising praziquantel, a macrolide lactone, cyclodextrin and a thickener - Google Patents
Anthelmintic paste comprising praziquantel, a macrolide lactone, cyclodextrin and a thickener Download PDFInfo
- Publication number
- CA2703008A1 CA2703008A1 CA2703008A CA2703008A CA2703008A1 CA 2703008 A1 CA2703008 A1 CA 2703008A1 CA 2703008 A CA2703008 A CA 2703008A CA 2703008 A CA2703008 A CA 2703008A CA 2703008 A1 CA2703008 A1 CA 2703008A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- paste according
- paste
- water
- cyclodextrin
- 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
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 35
- 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 32
- 229960002957 praziquantel Drugs 0.000 title claims abstract description 32
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 150000002596 lactones Chemical class 0.000 title claims abstract description 23
- 239000002562 thickening agent Substances 0.000 title claims abstract description 21
- 230000000507 anthelmentic effect Effects 0.000 title claims abstract description 15
- 239000003120 macrolide antibiotic agent Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 55
- 238000009472 formulation Methods 0.000 claims abstract description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 241001465754 Metazoa Species 0.000 claims abstract description 20
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 20
- 239000005660 Abamectin Substances 0.000 claims abstract description 12
- 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 claims abstract description 8
- 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 claims abstract description 8
- 244000079386 endoparasite Species 0.000 claims abstract description 6
- 241000282326 Felis catus Species 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 15
- CKVMAPHTVCTEMM-ALPQRHTBSA-N milbemycin oxime Chemical compound 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(=N/O)/[C@H]3OC\2)O)C[C@H]4C1.C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)C(=N/O)/[C@H]3OC\1)O)C[C@H]4C2 CKVMAPHTVCTEMM-ALPQRHTBSA-N 0.000 claims description 15
- 229940099245 milbemycin oxime Drugs 0.000 claims description 15
- 241000282472 Canis lupus familiaris Species 0.000 claims description 13
- 239000000796 flavoring agent Substances 0.000 claims description 11
- 235000019634 flavors Nutrition 0.000 claims description 11
- 239000004615 ingredient Substances 0.000 claims description 11
- 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 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- -1 glycol ethers Chemical class 0.000 claims description 7
- 239000003906 humectant Substances 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 239000003755 preservative agent Substances 0.000 claims description 7
- 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 claims description 6
- 230000005484 gravity Effects 0.000 claims description 6
- 229960002418 ivermectin Drugs 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003086 colorant Substances 0.000 claims description 5
- 239000003002 pH adjusting agent Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000009974 thixotropic effect Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- 229940074076 glycerol formal Drugs 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000010695 polyglycol Substances 0.000 claims description 2
- 229920000151 polyglycol Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 abstract description 9
- 150000003254 radicals Chemical class 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
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- 229920001285 xanthan gum Polymers 0.000 description 8
- 235000010493 xanthan gum Nutrition 0.000 description 8
- 229940082509 xanthan gum Drugs 0.000 description 8
- 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 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 229950008167 abamectin Drugs 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
- YZBLFMPOMVTDJY-LSGXYNIPSA-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-LSGXYNIPSA-N 0.000 description 4
- 235000015278 beef Nutrition 0.000 description 4
- 229940097362 cyclodextrins Drugs 0.000 description 4
- YNFMRVVYUVPIAN-AQUURSMBSA-N nemadectin Chemical compound C1[C@H](O)[C@H](C)[C@@H](C(/C)=C/C(C)C)O[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 YNFMRVVYUVPIAN-AQUURSMBSA-N 0.000 description 4
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 4
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- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 229940029985 mineral supplement Drugs 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229960005121 morantel Drugs 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- YSAUAVHXTIETRK-AATRIKPKSA-N pyrantel Chemical compound CN1CCCN=C1\C=C\C1=CC=CS1 YSAUAVHXTIETRK-AATRIKPKSA-N 0.000 description 1
- 229960005134 pyrantel Drugs 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
-
- 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
-
- 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
- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
-
- 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
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/724—Cyclodextrins
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07120767.4 | 2007-11-15 | ||
| EP07120767 | 2007-11-15 | ||
| PCT/EP2008/065335 WO2009062939A1 (en) | 2007-11-15 | 2008-11-12 | Anthelmintic paste comprising praziquantel, a macrolide lactone, cyclodextrin and a thickener |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2703008A1 true CA2703008A1 (en) | 2009-05-22 |
Family
ID=39092818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2703008A Abandoned CA2703008A1 (en) | 2007-11-15 | 2008-11-12 | Anthelmintic paste comprising praziquantel, a macrolide lactone, cyclodextrin and a thickener |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100286154A1 (enExample) |
| EP (1) | EP2219643B1 (enExample) |
| JP (1) | JP5319691B2 (enExample) |
| AU (1) | AU2008322995B2 (enExample) |
| CA (1) | CA2703008A1 (enExample) |
| ES (1) | ES2385126T3 (enExample) |
| WO (1) | WO2009062939A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201041508A (en) * | 2009-04-30 | 2010-12-01 | Dow Agrosciences Llc | Pesticide compositions exhibiting enhanced activity |
| GB2482526A (en) * | 2010-08-05 | 2012-02-08 | Fiona Anne Macdonald | Praziquantel suspendable powder as an immersion fish treatment for parasites |
| EP2594258B1 (en) * | 2011-11-18 | 2020-03-18 | Veterinärmedizinische Universität Wien | Oral gel comprising praziquantel |
| JP6499970B2 (ja) * | 2013-10-30 | 2019-04-10 | 大蔵製薬株式会社 | 服用し易いゼリー状医薬組成物 |
| GB2527555B (en) | 2014-06-25 | 2018-09-19 | Norbrook Lab Ltd | Stable methimazole liquid compositions |
| RU2613490C2 (ru) * | 2015-01-27 | 2017-03-16 | Общество с ограниченной ответственностью "Научно-производственная компания "СКиФФ" | Композиция на основе R(-)-празиквантела для лечения и профилактики гельминтозов у теплокровных |
| AU2017310506B2 (en) | 2016-08-11 | 2019-11-21 | Dmk Pharmaceuticals Corporation | Drug compositions |
| EP3720844A4 (en) | 2017-12-08 | 2021-08-11 | Adamis Pharmaceuticals Corporation | MEDICINAL COMPOSITIONS |
| DE102018002904A1 (de) | 2018-04-09 | 2019-10-10 | Marc de Cocq | Die Verwendung von Praziquantel in Kombination mit Milbemycinen zur Behandlung von Fischen |
| CN109432440B (zh) * | 2018-11-30 | 2022-04-26 | 佛山科学技术学院 | 一种吡喹酮羟丙基环糊精包合物及其制备方法和应用 |
| RU2722272C1 (ru) * | 2019-04-30 | 2020-05-28 | Общество с ограниченной ответственностью "Научно-производственная компания "СКиФФ" | Средство для лечения и профилактики нематодозов и цестодозов у мелких домашних животных |
| WO2022034226A1 (en) * | 2020-08-14 | 2022-02-17 | Universidad De Navarra | Avermectin and milbemycin compositions for inhalation |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4447414A (en) * | 1982-12-21 | 1984-05-08 | Cutter Laboratories, Inc. | Carnivore anthelmintics |
| SE9301489D0 (sv) * | 1993-04-30 | 1993-04-30 | Ab Astra | Veterinary composition |
| AUPM969994A0 (en) | 1994-11-28 | 1994-12-22 | Virbac S.A. | Equine anthelmintic formulations |
| EP0959891A1 (en) * | 1996-07-30 | 1999-12-01 | Ashmont Holdings Limited | Anthelmintic formulations |
| GB9801109D0 (en) | 1998-01-20 | 1998-03-18 | Pfizer | Cyclodextrin compositions |
| US6207179B1 (en) | 2000-05-18 | 2001-03-27 | Phoenix Scientific, Inc. | Parasiticidal formulation for animals and a method of making this formulation |
| US7704975B2 (en) * | 2000-12-19 | 2010-04-27 | Cephalon, Inc. | Modafinil compound and cyclodextrin mixtures |
| PL372341A1 (en) * | 2002-03-08 | 2005-07-11 | Bayer Business Services Gmbh | Antiparasitic artemisinin derivatives (endoperoxides) |
| US20060205681A1 (en) * | 2002-06-21 | 2006-09-14 | Maryam Moaddeb | Homogenous paste formulations |
| US7001889B2 (en) | 2002-06-21 | 2006-02-21 | Merial Limited | Anthelmintic oral homogeneous veterinary pastes |
| US20040151759A1 (en) * | 2002-08-16 | 2004-08-05 | Douglas Cleverly | Non-animal product containing veterinary formulations |
| CA2565159A1 (en) * | 2004-05-06 | 2005-12-15 | Cydex, Inc. | Taste-masked formulations containing sertraline and sulfoalkyl ether cyclodextrin |
| DE602005020796D1 (de) * | 2004-07-22 | 2010-06-02 | Bend Res Inc | Geschmacksabdeckende formulierung mit einer retardierten wirkstoffformulierung und/oder schnell löslichem cyclodextrin |
| AU2007100254B4 (en) | 2007-03-29 | 2007-05-03 | Jurox Pty Ltd | Improved parasiticide paste |
-
2008
- 2008-11-12 ES ES08850197T patent/ES2385126T3/es active Active
- 2008-11-12 WO PCT/EP2008/065335 patent/WO2009062939A1/en not_active Ceased
- 2008-11-12 JP JP2010533558A patent/JP5319691B2/ja not_active Expired - Fee Related
- 2008-11-12 CA CA2703008A patent/CA2703008A1/en not_active Abandoned
- 2008-11-12 AU AU2008322995A patent/AU2008322995B2/en not_active Ceased
- 2008-11-12 EP EP08850197A patent/EP2219643B1/en not_active Not-in-force
- 2008-11-12 US US12/742,257 patent/US20100286154A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011503140A (ja) | 2011-01-27 |
| JP5319691B2 (ja) | 2013-10-16 |
| AU2008322995B2 (en) | 2014-01-30 |
| AU2008322995A1 (en) | 2009-05-22 |
| WO2009062939A1 (en) | 2009-05-22 |
| US20100286154A1 (en) | 2010-11-11 |
| EP2219643A1 (en) | 2010-08-25 |
| ES2385126T3 (es) | 2012-07-18 |
| EP2219643B1 (en) | 2012-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20131010 |
|
| FZDE | Discontinued |
Effective date: 20161114 |