IE52364B1 - Anthelmintic composition and the use thereof - Google Patents
Anthelmintic composition and the use thereofInfo
- Publication number
- IE52364B1 IE52364B1 IE369/82A IE36982A IE52364B1 IE 52364 B1 IE52364 B1 IE 52364B1 IE 369/82 A IE369/82 A IE 369/82A IE 36982 A IE36982 A IE 36982A IE 52364 B1 IE52364 B1 IE 52364B1
- Authority
- IE
- Ireland
- Prior art keywords
- ami
- chloro
- composition
- benzimidazole
- anthelmintic
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 230000000507 anthelmentic effect Effects 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 20
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229940124339 anthelmintic agent Drugs 0.000 claims abstract description 17
- 239000000921 anthelmintic agent Substances 0.000 claims abstract description 17
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 16
- 229940088710 antibiotic agent Drugs 0.000 claims abstract description 16
- 229960000581 salicylamide Drugs 0.000 claims abstract description 15
- 239000003120 macrolide antibiotic agent Substances 0.000 claims abstract description 6
- HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 claims description 9
- 150000002537 isoquinolines Chemical class 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- LVUAENLZESTIDI-UHFFFAOYSA-N 6-chloro-5-(2,4-dichlorophenoxy)-2-methylsulfanyl-1h-benzimidazole Chemical compound C1=C2NC(SC)=NC2=CC(Cl)=C1OC1=CC=C(Cl)C=C1Cl LVUAENLZESTIDI-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 abstract 1
- 244000045947 parasite Species 0.000 description 17
- 241001465754 Metazoa Species 0.000 description 11
- 241000282472 Canis lupus familiaris Species 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229960002669 albendazole Drugs 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 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 description 7
- 229960001920 niclosamide Drugs 0.000 description 7
- RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 description 7
- 229960002957 praziquantel Drugs 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 6
- -1 B-41 series compounds Chemical class 0.000 description 5
- 241000283707 Capra Species 0.000 description 5
- 241000187747 Streptomyces Species 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- 241000242541 Trematoda Species 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 241001147672 Ancylostoma caninum Species 0.000 description 3
- 241000935792 Dipylidium caninum Species 0.000 description 3
- 241000243974 Haemonchus contortus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- 241000243794 Ostertagia ostertagi Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000244030 Toxocara canis Species 0.000 description 3
- 241001638368 Trichuris vulpis Species 0.000 description 3
- 210000003608 fece Anatomy 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241001126268 Cooperia Species 0.000 description 2
- 241001147667 Dictyocaulus Species 0.000 description 2
- 241000244160 Echinococcus Species 0.000 description 2
- 241000242711 Fasciola hepatica Species 0.000 description 2
- 241000243976 Haemonchus Species 0.000 description 2
- 241001137882 Nematodirus Species 0.000 description 2
- 241000510960 Oesophagostomum Species 0.000 description 2
- 238000011888 autopsy Methods 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 241001147657 Ancylostoma Species 0.000 description 1
- 241000204727 Ascaridia Species 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000931178 Bunostomum Species 0.000 description 1
- 241000253350 Capillaria Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- 241001327965 Clonorchis sinensis Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000935794 Dipylidium Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000144295 Eurytrema Species 0.000 description 1
- 241000144291 Eurytrema pancreaticum Species 0.000 description 1
- 241000204939 Fasciola gigantica Species 0.000 description 1
- 241001263042 Fasciola sp. Species 0.000 description 1
- 241001126302 Fasciolopsis buski Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000567920 Filariidae Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 241000404582 Hymenolepis <angiosperm> Species 0.000 description 1
- 241001464384 Hymenolepis nana Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001626715 Moniezia benedeni Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 241000904715 Oxyuris Species 0.000 description 1
- 241001480233 Paragonimus Species 0.000 description 1
- 241000244187 Parascaris Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000364057 Peoria Species 0.000 description 1
- 241000242678 Schistosoma Species 0.000 description 1
- 241000242677 Schistosoma japonicum Species 0.000 description 1
- 241000242680 Schistosoma mansoni Species 0.000 description 1
- 241000232199 Setariidae Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000122932 Strongylus Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241000244159 Taenia saginata Species 0.000 description 1
- 241000607216 Toxascaris Species 0.000 description 1
- 241000244031 Toxocara Species 0.000 description 1
- 241001489151 Trichuris Species 0.000 description 1
- 241000571986 Uncinaria Species 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 208000006275 fascioliasis Diseases 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 210000001365 lymphatic vessel Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- JYWIYHUXVMAGLG-UHFFFAOYSA-N oxyclozanide Chemical compound OC1=C(Cl)C=C(Cl)C=C1NC(=O)C1=C(O)C(Cl)=CC(Cl)=C1Cl JYWIYHUXVMAGLG-UHFFFAOYSA-N 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 210000000253 proventriculus Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- A61K31/60—Salicylic acid; Derivatives thereof
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- 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)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56025058A JPS57139012A (en) | 1981-02-23 | 1981-02-23 | Anthelmintic composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE820369L IE820369L (en) | 1982-08-23 |
| IE52364B1 true IE52364B1 (en) | 1987-09-30 |
Family
ID=12155318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE369/82A IE52364B1 (en) | 1981-02-23 | 1982-02-22 | Anthelmintic composition and the use thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4468390A (enExample) |
| EP (1) | EP0059074B1 (enExample) |
| JP (1) | JPS57139012A (enExample) |
| AU (1) | AU552403B2 (enExample) |
| DE (2) | DE3260921D1 (enExample) |
| GB (1) | GB2093695B (enExample) |
| IE (1) | IE52364B1 (enExample) |
| NL (1) | NL300082I1 (enExample) |
| NZ (1) | NZ199817A (enExample) |
| ZA (1) | ZA821135B (enExample) |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2753377B1 (fr) * | 1996-09-19 | 1999-09-24 | Rhone Merieux | Nouvelle association parasiticide a base de 1-n-phenylpyra- zoles et de lactones macrocycliques endectocides |
| US6426333B1 (en) * | 1996-09-19 | 2002-07-30 | Merial | Spot-on formulations for combating parasites |
| MA19678A1 (fr) * | 1982-01-13 | 1983-10-01 | Ciba Geigy Ag | Agents anti-helmintiques. |
| DE3410348A1 (de) * | 1984-03-21 | 1985-10-03 | Helmut Dr. Bozen Schwienbacher | Verfahren zur bekaempfung von fischmykosen und mittel zur durchfuehrung des verfahrens |
| ES2054962T3 (es) * | 1986-01-25 | 1994-08-16 | Hoechst Ag | Agentes plaguicidas. |
| GB9024924D0 (en) * | 1990-11-16 | 1991-01-02 | Beecham Group Plc | Novel compositions |
| AU2003236405B2 (en) * | 1999-04-14 | 2007-10-25 | Merial Ltd | Anthelmintic Composition |
| NZ335166A (en) | 1999-04-14 | 2001-11-30 | Ashmont Holdings Ltd | Anthelmintic composition containing triclabendazole in at least one solvent |
| AUPM969994A0 (en) | 1994-11-28 | 1994-12-22 | Virbac S.A. | Equine anthelmintic formulations |
| AU691990B2 (en) * | 1994-11-28 | 1998-05-28 | Virbac S.A. | Equine anthelmintic formulations |
| DE19520275A1 (de) * | 1995-06-02 | 1996-12-05 | Bayer Ag | Endoparasitizide Mittel |
| 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 |
| US6214367B1 (en) | 1996-06-05 | 2001-04-10 | Ashmont Holdings Limited | Injectable compositions |
| DE19654079A1 (de) | 1996-12-23 | 1998-06-25 | Bayer Ag | Endo-ekto-parasitizide Mittel |
| ES2359973T3 (es) | 1998-03-19 | 2011-05-30 | MERCK SHARP & DOHME CORP. | Composiciones poliméricas líquidas para la liberación controlada de sustancias bioactivas. |
| US6893652B2 (en) | 2001-08-27 | 2005-05-17 | Wyeth | Endoparasiticidal gel composition |
| US7001889B2 (en) * | 2002-06-21 | 2006-02-21 | Merial Limited | Anthelmintic oral homogeneous veterinary pastes |
| US20060205681A1 (en) * | 2002-06-21 | 2006-09-14 | Maryam Moaddeb | Homogenous paste formulations |
| US20040077703A1 (en) * | 2002-10-02 | 2004-04-22 | Soll Mark D. | Nodulisporic acid derivative spot-on formulations for combating parasites |
| AU2004228041B2 (en) * | 2003-04-04 | 2009-06-04 | Boehringer Ingelheim Animal Health USA Inc. | Topical anthelmintic veterinary formulations |
| JP4734498B2 (ja) * | 2003-07-09 | 2011-07-27 | ライフ テクノロジーズ コーポレイション | タンパク質−タンパク質相互作用を解析する方法 |
| US7396819B2 (en) | 2003-08-08 | 2008-07-08 | Virbac Corporation | Anthelmintic formulations |
| US7671034B2 (en) * | 2003-12-19 | 2010-03-02 | Merial Limited | Stabilized formulation of ivermectin feed premix with an extended shelf life |
| WO2005094210A2 (en) | 2004-03-12 | 2005-10-13 | The Hartz Mountain Corporation | Multi-action anthelmintic formulations |
| KR20070008686A (ko) * | 2004-04-07 | 2007-01-17 | 인터벳 인터내셔널 비.브이. | 벤지미다졸, 아버멕틴 및 프라지콴텔의 효능성 조성물 및이의 사용 방법 |
| GB0508993D0 (en) * | 2005-05-03 | 2005-06-08 | Syngenta Participations Ag | Pesticidal compositions |
| US8362086B2 (en) | 2005-08-19 | 2013-01-29 | Merial Limited | Long acting injectable formulations |
| US20080027011A1 (en) * | 2005-12-20 | 2008-01-31 | Hassan Nached | Homogeneous paste and gel formulations |
| NZ573758A (en) | 2006-07-05 | 2012-01-12 | Aventis Agriculture | 1-Phenyl-3-cyano-pyrazole derivatives and pesticidal formulations containing them |
| US7919522B2 (en) * | 2007-05-03 | 2011-04-05 | Merial Limited | Compositions comprising C-13 alkoxyether macrolide compounds and phenylpyrazole compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4914624A (enExample) * | 1972-06-08 | 1974-02-08 | ||
| PH15982A (en) * | 1977-10-03 | 1983-05-18 | Merck & Co Inc | Selective hydrogenation producta of c-076 compounds and derivatives thereof |
| US4144352A (en) * | 1977-12-19 | 1979-03-13 | Merck & Co., Inc. | Milbemycin compounds as anthelmintic agents |
| US4203976A (en) * | 1978-08-02 | 1980-05-20 | Merck & Co., Inc. | Sugar derivatives of C-076 compounds |
| US4289760A (en) * | 1980-05-02 | 1981-09-15 | Merck & Co., Inc. | 23-Keto derivatives of C-076 compounds |
-
1981
- 1981-02-23 JP JP56025058A patent/JPS57139012A/ja active Granted
-
1982
- 1982-02-18 EP EP82300829A patent/EP0059074B1/en not_active Expired
- 1982-02-18 GB GB8204765A patent/GB2093695B/en not_active Expired
- 1982-02-18 DE DE8282300829T patent/DE3260921D1/de not_active Expired
- 1982-02-18 DE DE2002199008 patent/DE10299008I2/de active Active
- 1982-02-22 IE IE369/82A patent/IE52364B1/en active Protection Beyond IP Right Term
- 1982-02-22 US US06/350,641 patent/US4468390A/en not_active Expired - Lifetime
- 1982-02-22 ZA ZA821135A patent/ZA821135B/xx unknown
- 1982-02-23 NZ NZ199817A patent/NZ199817A/en unknown
- 1982-02-23 AU AU80711/82A patent/AU552403B2/en not_active Expired
-
2002
- 2002-02-13 NL NL300082C patent/NL300082I1/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE820369L (en) | 1982-08-23 |
| AU552403B2 (en) | 1986-05-29 |
| GB2093695B (en) | 1984-03-28 |
| NZ199817A (en) | 1984-12-14 |
| EP0059074B1 (en) | 1984-10-10 |
| DE10299008I2 (de) | 2004-10-21 |
| AU8071182A (en) | 1982-09-02 |
| DE10299008I1 (de) | 2002-07-04 |
| US4468390A (en) | 1984-08-28 |
| NL300082I1 (nl) | 2002-04-02 |
| JPH0125722B2 (enExample) | 1989-05-19 |
| ZA821135B (en) | 1983-02-23 |
| JPS57139012A (en) | 1982-08-27 |
| EP0059074A1 (en) | 1982-09-01 |
| GB2093695A (en) | 1982-09-08 |
| DE3260921D1 (en) | 1984-11-15 |
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