CA2476520C - Long acting parasiticidal composition containing a salicylanilide compound, a polymeric species and at least one other anti-parasitic compound - Google Patents
Long acting parasiticidal composition containing a salicylanilide compound, a polymeric species and at least one other anti-parasitic compound Download PDFInfo
- Publication number
- CA2476520C CA2476520C CA002476520A CA2476520A CA2476520C CA 2476520 C CA2476520 C CA 2476520C CA 002476520 A CA002476520 A CA 002476520A CA 2476520 A CA2476520 A CA 2476520A CA 2476520 C CA2476520 C CA 2476520C
- Authority
- CA
- Canada
- Prior art keywords
- closantel
- ivermectin
- compound
- salicylanilide
- amount
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 150000001875 compounds Chemical class 0.000 title claims abstract description 13
- 229950000975 salicylanilide Drugs 0.000 title claims abstract description 10
- -1 salicylanilide compound Chemical class 0.000 title claims abstract description 7
- 239000003096 antiparasitic agent Substances 0.000 title claims description 22
- 230000002141 anti-parasite Effects 0.000 title claims description 8
- 230000000590 parasiticidal effect Effects 0.000 title description 9
- JMPFSEBWVLAJKM-UHFFFAOYSA-N N-{5-chloro-4-[(4-chlorophenyl)(cyano)methyl]-2-methylphenyl}-2-hydroxy-3,5-diiodobenzamide Chemical compound ClC=1C=C(NC(=O)C=2C(=C(I)C=C(I)C=2)O)C(C)=CC=1C(C#N)C1=CC=C(Cl)C=C1 JMPFSEBWVLAJKM-UHFFFAOYSA-N 0.000 claims abstract description 47
- 229950004178 closantel Drugs 0.000 claims abstract description 47
- 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 abstract description 40
- 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 abstract description 40
- 229960002418 ivermectin Drugs 0.000 claims abstract description 39
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 229940074076 glycerol formal Drugs 0.000 claims abstract description 16
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 15
- 239000005660 Abamectin Substances 0.000 claims abstract description 11
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 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 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract description 4
- 229920001400 block copolymer Polymers 0.000 claims abstract description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims abstract description 4
- 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 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 21
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 21
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 20
- 230000037058 blood plasma level Effects 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims 1
- 244000045947 parasite Species 0.000 abstract description 14
- 239000002202 Polyethylene glycol Substances 0.000 abstract description 13
- 241001465754 Metazoa Species 0.000 abstract description 12
- 241000894007 species Species 0.000 abstract description 6
- 210000002381 plasma Anatomy 0.000 abstract 1
- 238000009472 formulation Methods 0.000 description 35
- 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 description 12
- 238000012360 testing method Methods 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 244000078703 ectoparasite Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 4
- 244000144972 livestock Species 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013066 combination product Substances 0.000 description 3
- 229940127555 combination product Drugs 0.000 description 3
- 244000079386 endoparasite Species 0.000 description 3
- 239000007972 injectable composition Substances 0.000 description 3
- 239000003182 parenteral nutrition solution Substances 0.000 description 3
- 239000004540 pour-on Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 2
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 2
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000013011 aqueous formulation Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000001720 carbohydrates Chemical group 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229960001614 levamisole Drugs 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000002297 parasiticide Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VARHUCVRRNANBD-PVVXTEPVSA-N 22,23-dihydroavermectin B1b 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 VARHUCVRRNANBD-PVVXTEPVSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- NQPDXQQQCQDHHW-UHFFFAOYSA-N 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole Chemical compound ClC=1C=C2NC(SC)=NC2=CC=1OC1=CC=CC(Cl)=C1Cl NQPDXQQQCQDHHW-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 241000242711 Fasciola hepatica Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- 241001468227 Streptomyces avermitilis Species 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 229940125687 antiparasitic agent Drugs 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 208000006275 fascioliasis Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- FSVSNKCOMJVGLM-UHFFFAOYSA-N octanoic acid;propane-1,2-diol Chemical class CC(O)CO.CCCCCCCC(O)=O FSVSNKCOMJVGLM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229960000323 triclabendazole Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- 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
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0204712.4 | 2002-02-28 | ||
| GB0204712A GB2386066A (en) | 2002-02-28 | 2002-02-28 | Long-acting parasiticidal composition with improved bioavailability comprising a salicylanilide, a further anti-parasitic compound & a polymeric species |
| PCT/GB2003/000645 WO2003072113A1 (en) | 2002-02-28 | 2003-02-12 | Long acting parasiticidal composition containing a salicylanilide compound, a polymeric species and at least one other anti-parasitic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2476520A1 CA2476520A1 (en) | 2003-09-04 |
| CA2476520C true CA2476520C (en) | 2009-08-11 |
Family
ID=9931978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002476520A Expired - Lifetime CA2476520C (en) | 2002-02-28 | 2003-02-12 | Long acting parasiticidal composition containing a salicylanilide compound, a polymeric species and at least one other anti-parasitic compound |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US9289380B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1478372B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4480400B2 (cg-RX-API-DMAC7.html) |
| AP (1) | AP1977A (cg-RX-API-DMAC7.html) |
| AR (1) | AR038852A1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE347897T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2003205887B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR0307974B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2476520C (cg-RX-API-DMAC7.html) |
| CO (1) | CO5611154A2 (cg-RX-API-DMAC7.html) |
| CR (1) | CR7429A (cg-RX-API-DMAC7.html) |
| CY (1) | CY1107530T1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE60310377T2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK1478372T3 (cg-RX-API-DMAC7.html) |
| EC (1) | ECSP045320A (cg-RX-API-DMAC7.html) |
| ES (1) | ES2275076T3 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2386066A (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA04007996A (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ534704A (cg-RX-API-DMAC7.html) |
| PT (1) | PT1478372E (cg-RX-API-DMAC7.html) |
| SI (1) | SI1478372T1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2003072113A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200406782B (cg-RX-API-DMAC7.html) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002952597A0 (en) * | 2002-11-11 | 2002-11-28 | Schering-Plough Pty. Limited | Topical parasiticide formulations and methods of treatment |
| US7731947B2 (en) | 2003-11-17 | 2010-06-08 | Intarcia Therapeutics, Inc. | Composition and dosage form comprising an interferon particle formulation and suspending vehicle |
| RU2005133427A (ru) | 2003-03-31 | 2006-04-27 | Алза Корпорейшн (Us) | Безводные однофазные носители и препараты с использованием таких носителей |
| US7666444B2 (en) | 2004-02-02 | 2010-02-23 | Wyeth | Antiparasitic composition |
| EP1824474A1 (en) * | 2004-12-10 | 2007-08-29 | Bayer HealthCare AG | Anthelmintic composition |
| WO2006083761A2 (en) | 2005-02-03 | 2006-08-10 | Alza Corporation | Solvent/polymer solutions as suspension vehicles |
| US11246913B2 (en) | 2005-02-03 | 2022-02-15 | Intarcia Therapeutics, Inc. | Suspension formulation comprising an insulinotropic peptide |
| US20070027105A1 (en) | 2005-07-26 | 2007-02-01 | Alza Corporation | Peroxide removal from drug delivery vehicle |
| ES2351527T3 (es) | 2006-05-30 | 2011-02-07 | Intarcia Therapeutics, Inc | Modulador de flujo en dos piezas con conducto interno para un sistema osmótico de administración. |
| KR101200728B1 (ko) | 2006-08-09 | 2012-11-13 | 인타르시아 세라퓨틱스 인코포레이티드 | 삼투성 전달 시스템 및 피스톤 조립체 |
| RU2440097C2 (ru) | 2007-04-23 | 2012-01-20 | Интарсия Терапьютикс, Инк. | Способ лечения диабета ii типа и ожирения, осмотическое устройство для доставки и способ его изготовления |
| CA2726861C (en) | 2008-02-13 | 2014-05-27 | Intarcia Therapeutics, Inc. | Devices, formulations, and methods for delivery of multiple beneficial agents |
| HRP20171801T1 (hr) | 2009-09-28 | 2017-12-29 | Intarcia Therapeutics, Inc. | Brzo uspostavljanje i/ili brzo završavanje uglavnom stabilne primjene lijeka |
| US20120208755A1 (en) | 2011-02-16 | 2012-08-16 | Intarcia Therapeutics, Inc. | Compositions, Devices and Methods of Use Thereof for the Treatment of Cancers |
| FR2991173B1 (fr) | 2012-06-04 | 2015-11-06 | Virbac | Composition veterinaire a administration cutanee a base d'oxyclozanide |
| CN105579029B (zh) * | 2013-09-30 | 2019-03-05 | 硕腾服务有限责任公司 | 长效螺异恶唑啉制剂 |
| ES2661000T3 (es) | 2014-09-12 | 2018-03-27 | Antibiotx A/S | Uso antibacteriano de salicilanilidas halogenadas |
| US9889085B1 (en) | 2014-09-30 | 2018-02-13 | Intarcia Therapeutics, Inc. | Therapeutic methods for the treatment of diabetes and related conditions for patients with high baseline HbA1c |
| GB201509326D0 (en) | 2015-05-29 | 2015-07-15 | Antibio Tx Aps | Novel use |
| CN113598842A (zh) | 2015-06-03 | 2021-11-05 | 因塔西亚制药公司 | 植入物放置和移除系统 |
| GB201604484D0 (en) * | 2016-03-16 | 2016-04-27 | Antibiotx Aps And Københavns Uni University Of Copenhagen | Topical antibacterial compositions |
| RU2760007C2 (ru) | 2016-05-16 | 2021-11-22 | Интарсия Терапьютикс, Инк. | Полипептиды, селективные к рецепторам глюкагона, и способы их применения |
| USD860451S1 (en) | 2016-06-02 | 2019-09-17 | Intarcia Therapeutics, Inc. | Implant removal tool |
| USD840030S1 (en) | 2016-06-02 | 2019-02-05 | Intarcia Therapeutics, Inc. | Implant placement guide |
| WO2018129058A1 (en) | 2017-01-03 | 2018-07-12 | Intarcia Therapeutics, Inc. | Methods comprising continuous administration of a glp-1 receptor agonist and co-adminstration of a drug |
| US11419834B2 (en) | 2019-02-25 | 2022-08-23 | Rhode Island Hospital | Methods for treating diseases or infections caused by or associated with H. pylori using a halogenated salicylanilide |
| BR112022013784A2 (pt) | 2020-01-13 | 2022-10-11 | Durect Corp | Sistemas de distribuição de fármacos de liberação prolongada com impurezas reduzidas e métodos relacionados |
| JP2024503402A (ja) | 2021-01-12 | 2024-01-25 | デュレクト コーポレーション | 徐放性薬物送達システム及び関連の方法 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950360A (en) | 1972-06-08 | 1976-04-13 | Sankyo Company Limited | Antibiotic substances |
| DE2263509C2 (de) | 1972-12-27 | 1981-12-24 | Rudolf Dr. 6380 Bad Homburg Kürner | Deodorant |
| US4005218A (en) * | 1975-03-18 | 1977-01-25 | Janssen Pharmaceutica N.V. | Antiparasitic salicylanilide derivatives |
| SE434277B (sv) * | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
| US4206205A (en) * | 1977-10-03 | 1980-06-03 | Merck & Co., Inc. | Monosaccharide and aglycone derivatives of C-076 |
| US4199569A (en) * | 1977-10-03 | 1980-04-22 | Merck & Co., Inc. | Selective hydrogenation products of C-076 compounds and derivatives thereof |
| US4173571A (en) * | 1977-12-19 | 1979-11-06 | Merck & Co., Inc. | 13-Halo and 13-deoxy derivatives of C-076 compounds |
| US4171314A (en) * | 1977-12-19 | 1979-10-16 | Merck & Co., Inc. | 13-Halo and 13-deoxy C-076 compounds |
| US4128632A (en) * | 1978-02-13 | 1978-12-05 | Merck & Co., Inc. | Solubilization of Rafoxanide |
| OA06863A (fr) | 1980-08-04 | 1983-02-28 | Merck & Co Inc | Solubilisation de l'invermectine dans l'eau. |
| NZ210505A (en) | 1983-12-22 | 1988-06-30 | Merck & Co Inc | Parasiticidal compositions containing avermectin or milbemycin derivatives |
| GB8727157D0 (en) * | 1987-11-19 | 1987-12-23 | Wellcome Found | Pharmaceutical formulations |
| NZ223200A (en) * | 1988-01-15 | 1989-01-06 | Ancare Distributors | Anthelmintic compositions containing 2',5-dicloro-4'-nitrosalicylanilide and non aqueous carrier |
| US5273805A (en) * | 1991-08-05 | 1993-12-28 | Minnesota Mining And Manufacturing Company | Structured flexible carrier web with recess areas bearing a layer of silicone on predetermined surfaces |
| NZ335166A (en) | 1999-04-14 | 2001-11-30 | Ashmont Holdings Ltd | Anthelmintic composition containing triclabendazole in at least one solvent |
| CN1054504C (zh) | 1993-03-15 | 2000-07-19 | 科尔加特·帕尔莫利弗公司 | 洁牙剂 |
| PL174488B1 (pl) | 1993-05-10 | 1998-08-31 | Merck & Co Inc | Preparat do zwalczania pasożytów zwierząt oraz sposób wytwarzania preparatu do zwalczania pasożytów zwierząt |
| DE69432985D1 (de) | 1993-06-15 | 2003-09-04 | Australian Nat University Acto | Synergistische anthelmintische zusammensetzungen gegen fasciola hepatica und andere fascola spezien |
| NZ248486A (en) * | 1993-08-24 | 1996-07-26 | Ashmont Holdings Limited Subst | Stable anthelmintic formulation containing closantel and one or more avermectins or milbemycins in a glycol based solvent |
| WO1995016447A1 (en) | 1993-12-13 | 1995-06-22 | Michael Hilary Burke | Anthelmintic composition containing rafoxanide and fenbendazole |
| FR2739778B1 (fr) | 1995-10-13 | 1997-12-12 | Virbac Lab | Formulation topique destinee a traiter la maladie de la douve du foie chez l'animal |
| US5773422A (en) * | 1996-01-29 | 1998-06-30 | Komer; Gene | Avermectin formulation |
| US6193989B1 (en) * | 1997-03-21 | 2001-02-27 | Biogenesis S.A. | Long acting injectable parasiticidal composition and the process for its preparation |
| US6340672B1 (en) | 2000-02-16 | 2002-01-22 | Phoenix Scientific, Inc. | Parasiticidal formulation and a method of making this formulation |
| AUPQ875700A0 (en) * | 2000-07-13 | 2000-08-03 | Reflex Research Limited | Combination compositions |
| AUPR510001A0 (en) | 2001-05-18 | 2001-06-14 | Jupitar Pty Ltd | Formulation and method |
-
2002
- 2002-02-28 GB GB0204712A patent/GB2386066A/en not_active Withdrawn
-
2003
- 2003-02-12 BR BRPI0307974-0B1A patent/BR0307974B1/pt not_active IP Right Cessation
- 2003-02-12 ES ES03702765T patent/ES2275076T3/es not_active Expired - Lifetime
- 2003-02-12 DK DK03702765T patent/DK1478372T3/da active
- 2003-02-12 NZ NZ534704A patent/NZ534704A/en not_active IP Right Cessation
- 2003-02-12 US US10/504,331 patent/US9289380B2/en active Active
- 2003-02-12 MX MXPA04007996A patent/MXPA04007996A/es active IP Right Grant
- 2003-02-12 WO PCT/GB2003/000645 patent/WO2003072113A1/en not_active Ceased
- 2003-02-12 EP EP03702765A patent/EP1478372B1/en not_active Expired - Lifetime
- 2003-02-12 JP JP2003570859A patent/JP4480400B2/ja not_active Expired - Lifetime
- 2003-02-12 DE DE60310377T patent/DE60310377T2/de not_active Expired - Lifetime
- 2003-02-12 AP APAP/P/2004/003142A patent/AP1977A/en active
- 2003-02-12 AU AU2003205887A patent/AU2003205887B2/en not_active Expired
- 2003-02-12 PT PT03702765T patent/PT1478372E/pt unknown
- 2003-02-12 SI SI200330637T patent/SI1478372T1/sl unknown
- 2003-02-12 CA CA002476520A patent/CA2476520C/en not_active Expired - Lifetime
- 2003-02-12 AT AT03702765T patent/ATE347897T1/de active
- 2003-02-27 AR ARP030100640A patent/AR038852A1/es not_active Application Discontinuation
-
2004
- 2004-08-24 CR CR7429A patent/CR7429A/es unknown
- 2004-08-26 ZA ZA2004/06782A patent/ZA200406782B/en unknown
- 2004-09-14 CO CO04091274A patent/CO5611154A2/es not_active Application Discontinuation
- 2004-09-28 EC EC2004005320A patent/ECSP045320A/es unknown
-
2007
- 2007-01-10 CY CY20071100037T patent/CY1107530T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR038852A1 (es) | 2005-01-26 |
| GB2386066A (en) | 2003-09-10 |
| ATE347897T1 (de) | 2007-01-15 |
| MXPA04007996A (es) | 2004-11-26 |
| AU2003205887B2 (en) | 2007-02-15 |
| NZ534704A (en) | 2007-02-23 |
| BR0307974B1 (pt) | 2014-10-21 |
| DE60310377T2 (de) | 2007-10-31 |
| ECSP045320A (es) | 2004-11-26 |
| AP2004003142A0 (en) | 2004-09-30 |
| US9289380B2 (en) | 2016-03-22 |
| SI1478372T1 (sl) | 2007-04-30 |
| GB0204712D0 (en) | 2002-04-17 |
| JP4480400B2 (ja) | 2010-06-16 |
| CY1107530T1 (el) | 2013-03-13 |
| AP1977A (en) | 2009-03-19 |
| WO2003072113A1 (en) | 2003-09-04 |
| ZA200406782B (en) | 2005-07-27 |
| CA2476520A1 (en) | 2003-09-04 |
| EP1478372A1 (en) | 2004-11-24 |
| DK1478372T3 (da) | 2007-04-10 |
| AU2003205887A1 (en) | 2003-09-09 |
| DE60310377D1 (de) | 2007-01-25 |
| JP2005525355A (ja) | 2005-08-25 |
| BR0307974A (pt) | 2004-12-21 |
| CO5611154A2 (es) | 2006-02-28 |
| EP1478372B1 (en) | 2006-12-13 |
| PT1478372E (pt) | 2007-01-31 |
| ES2275076T3 (es) | 2007-06-01 |
| CR7429A (es) | 2006-02-06 |
| US20050118221A1 (en) | 2005-06-02 |
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