IE60375B1 - A method for producing a veterinary curative and for processing it into a pharmaceutically acceptable form - Google Patents
A method for producing a veterinary curative and for processing it into a pharmaceutically acceptable formInfo
- Publication number
- IE60375B1 IE60375B1 IE220187A IE220187A IE60375B1 IE 60375 B1 IE60375 B1 IE 60375B1 IE 220187 A IE220187 A IE 220187A IE 220187 A IE220187 A IE 220187A IE 60375 B1 IE60375 B1 IE 60375B1
- Authority
- IE
- Ireland
- Prior art keywords
- veterinary
- cattle
- remedy
- cyanomethyl
- liquid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 241000283690 Bos taurus Species 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 244000045947 parasite Species 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 6
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 241001494479 Pecora Species 0.000 claims description 5
- 229960001614 levamisole Drugs 0.000 claims description 5
- 241000283707 Capra Species 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 3
- 230000003449 preventive effect Effects 0.000 claims description 3
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 3
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 3
- 229960003415 propylparaben Drugs 0.000 claims description 3
- 239000001509 sodium citrate Substances 0.000 claims description 3
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 4
- 230000002141 anti-parasite Effects 0.000 claims 2
- 239000003096 antiparasitic agent Substances 0.000 claims 2
- ORECNKBJIMKZNX-UHFFFAOYSA-N 1,3-thiazol-3-ium;chloride Chemical compound Cl.C1=CSC=N1 ORECNKBJIMKZNX-UHFFFAOYSA-N 0.000 claims 1
- 241000282898 Sus scrofa Species 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims 1
- 235000012239 silicon dioxide Nutrition 0.000 claims 1
- LDTLADDKFLAYJA-UHFFFAOYSA-L sodium metabisulphite Chemical compound [Na+].[Na+].[O-]S(=O)OS([O-])=O LDTLADDKFLAYJA-UHFFFAOYSA-L 0.000 claims 1
- 235000010262 sodium metabisulphite Nutrition 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 244000078703 ectoparasite Species 0.000 abstract description 3
- 244000144972 livestock Species 0.000 abstract description 2
- 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 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 6
- 241000238421 Arthropoda Species 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 5
- SAPZSIZFEJFOFN-UHFFFAOYSA-N 2,3-diiodobenzamide Chemical class NC(=O)C1=CC=CC(I)=C1I SAPZSIZFEJFOFN-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 2
- 241000243976 Haemonchus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 241000869417 Trematodes Species 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000001418 larval effect Effects 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- SAUCCHYJIUFNEJ-UHFFFAOYSA-N 2-phenyl-2h-imidazo[4,5-d][1,3]thiazole Chemical class N1=C2N=CN=C2SC1C1=CC=CC=C1 SAUCCHYJIUFNEJ-UHFFFAOYSA-N 0.000 description 1
- SQFLFRQWPBEDHM-UHFFFAOYSA-N 4-chloro-1-methyl-2-nitrobenzene Chemical compound CC1=CC=C(Cl)C=C1[N+]([O-])=O SQFLFRQWPBEDHM-UHFFFAOYSA-N 0.000 description 1
- OHISOIJFGZHSCW-UHFFFAOYSA-N 6-phenyl-3,5-dihydroimidazo[4,5-c][1,2]thiazole;hydrochloride Chemical compound Cl.C1N=C2CSN=C2N1C1=CC=CC=C1 OHISOIJFGZHSCW-UHFFFAOYSA-N 0.000 description 1
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 1
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- 241000283725 Bos Species 0.000 description 1
- 241001307956 Chorioptes bovis Species 0.000 description 1
- 241000202828 Dermatobia hominis Species 0.000 description 1
- 241001547356 Hyostrongylus rubidus Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 241000543830 Hypoderma bovis Species 0.000 description 1
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000243789 Metastrongyloidea Species 0.000 description 1
- 241001181140 Metastrongylus apri Species 0.000 description 1
- 241000862461 Oesophagostomum dentatum Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001649230 Psoroptes ovis Species 0.000 description 1
- 241000864246 Rhipicephalus decoloratus Species 0.000 description 1
- 241000244174 Strongyloides Species 0.000 description 1
- 241001489151 Trichuris Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 231100000195 subchronic toxicity Toxicity 0.000 description 1
- 230000007666 subchronic toxicity Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000002211 ultraviolet spectrum 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
- A61K31/41—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
- A61K31/425—Thiazoles
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8603150A NL8603150A (nl) | 1986-12-11 | 1986-12-11 | Preventief en therapeutisch preparaat tegen parasieten, alsmede werkwijze ter bereiding daarvan. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE872201L IE872201L (en) | 1988-06-11 |
| IE60375B1 true IE60375B1 (en) | 1994-07-13 |
Family
ID=19848979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE220187A IE60375B1 (en) | 1986-12-11 | 1987-08-18 | A method for producing a veterinary curative and for processing it into a pharmaceutically acceptable form |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0272706B1 (enrdf_load_stackoverflow) |
| DE (1) | DE3782408D1 (enrdf_load_stackoverflow) |
| ES (1) | ES2052547T3 (enrdf_load_stackoverflow) |
| GR (1) | GR3006126T3 (enrdf_load_stackoverflow) |
| IE (1) | IE60375B1 (enrdf_load_stackoverflow) |
| NL (2) | NL8603150A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2801791B1 (fr) * | 1999-12-03 | 2003-05-30 | Elpronat | Composition pour animaux contenant du salicylate de methyle |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU527154B2 (en) * | 1978-12-15 | 1983-02-17 | Pitman-Moore Australia Limited | Composition and process |
-
1986
- 1986-12-11 NL NL8603150A patent/NL8603150A/nl not_active Application Discontinuation
-
1987
- 1987-07-13 ES ES87201320T patent/ES2052547T3/es not_active Expired - Lifetime
- 1987-07-13 DE DE8787201320T patent/DE3782408D1/de not_active Expired - Lifetime
- 1987-07-13 EP EP87201320A patent/EP0272706B1/de not_active Expired - Lifetime
- 1987-08-18 IE IE220187A patent/IE60375B1/en not_active IP Right Cessation
-
1992
- 1992-11-02 GR GR920402462T patent/GR3006126T3/el unknown
-
1993
- 1993-06-17 NL NL930076C patent/NL930076I1/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0272706A2 (de) | 1988-06-29 |
| NL8603150A (nl) | 1988-07-01 |
| ES2052547T3 (es) | 1994-07-16 |
| EP0272706A3 (en) | 1990-02-07 |
| NL930076I1 (nl) | 1993-09-16 |
| EP0272706B1 (de) | 1992-10-28 |
| IE872201L (en) | 1988-06-11 |
| DE3782408D1 (de) | 1992-12-03 |
| GR3006126T3 (enrdf_load_stackoverflow) | 1993-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |