IE56522B1 - Agent for coccidiosis - Google Patents
Agent for coccidiosisInfo
- Publication number
- IE56522B1 IE56522B1 IE47/84A IE4784A IE56522B1 IE 56522 B1 IE56522 B1 IE 56522B1 IE 47/84 A IE47/84 A IE 47/84A IE 4784 A IE4784 A IE 4784A IE 56522 B1 IE56522 B1 IE 56522B1
- Authority
- IE
- Ireland
- Prior art keywords
- water
- solution according
- miscible solution
- miscible
- methyl
- Prior art date
Links
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
- A61K9/10—Dispersions; Emulsions
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- 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
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
- Peptides Or Proteins (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Enzymes And Modification Thereof (AREA)
- Feed For Specific Animals (AREA)
- Fodder In General (AREA)
- Cosmetics (AREA)
- Magnetic Record Carriers (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
1. Water-miscible solutions of 1-[3-methyl-4-(4'-trifluoromethyl- -thiophenoxy)-phenyl]-3-methyl-1,3,5-triazine-2,4,6-(1- H, 3H, 5H)-trione, characterized in that they contain one or more polar solvents and have an alkaline reaction.
Description
The Invention relates to water-miscible solutions of 1-C3-methyl-4-<4e-trifluoromethyIthiophenoxy)pheny133-methy1-1,3,5-tria2in-2,4,6(1H,3H,5H)-trlone and their use for controlling coccidiosis.
The abovementioned compound, the chemicaL structural formula of which is shown below. is known as an active compound for coccidiosis illnesses and similar illnesses in animals. For treatment, this active compound has hitherto been added in a Billed crystalline form to the animal feed. However, no utilisable form for administration has hitherto been found for treatment via the drinking water, for which there is a great demand in many places. In order to ensure reliable notl15 fication via the drinking water, an active compound of this type shouLd be present in homogeneous distribution in water for about 24 hours. The active compound only dissolves to the extent of about 5 ppm in water, that 1s to say insufficiently. Introduced as a suspension, at the concentration for administration, it sediments out in this period.
The concentration for administration can, depending on the severity of the illness, be between 5 and 500 ppm, but is mostly between 20 and 200 ppm.
The active compound of the formula (I) is readily solubLe in a variety of organic solvents, such as, for example, acetone, ethyl lactate or N-methylpyrrolidone. However, on diluting a solution of this type, in drinking water for animals, to the concentration for administration, the active compound precipitates out Immediately or after a short time. Moreover, solubilisation with solubilisers, such as, for example, polyoxyethyLated castor oil or polyoxyethy lene-sorblten fatty acid esters does not lead to success. The precipitation of the active compound is certainly delayed by a few hours, but not for 24 hours, f It has now been found, surprisingly, that water* miscible solutions of the active compound of the formula \ (I) which contain one or more polar solvents and have an alkaline reaction can be diluted 1n the drinking water for the animals to the concentrations for administration and do not precipitate out over the course of 24 hours.
Accordingly, the Invention relates to water* miscible solutions of 1-C3-methy1-4-(41-trifluoromethyl15 th i oph.enoxy ) pheny 13-3-me thy 1-1,3, 5-tr lax In-2,4,6(1 H,3H,5H)trione, which contain one or more polar solvents and have an alkaline reaction.
For the preparation of the solutions according to the Invention, the active compound Is dissolved In a polar water-soluble solvent which either has an alkaline reaction or to which a water-soluble alkaline substance Is added. The latter Is more advantageously likewise dissolved In the solvent, but It can also be suspended In the solvent and only dissolve 1n the drinking water. In this connec25 tion, the drinking water should have a pH above 7, but preferably a pH above 8, after addition of the soLutlon of active compound.
The solution of the concentrate of active compound should not have a pH above 11 nor have a pH below 8.
The concentration of the active compound can be In the range 0.5-50%, but 1s preferably In a range of 1-25%.
Suitable solvents are all water-soluble solvents In which the active compound dissolves to give an adequate concentration and which are physiologically acceptable.
These comprise, from the series of alcohols, mono* hydric and polyhydrlc, such as, for example, ethyl alcohol, Isopropyl alcohol, benzyl alcohol, glycerol, propylene glycol, poLyethylene glycols, poly(oxoethylene)-poly(oxypropylene) polymers, and basic alcohols, such as, for example, mono-, di- and triethanolamine.
Ketones are also suitable, for example acetone or methyl ethyl ketone and, from the series of esters, y for example, ethyl lactate. Other solvents, such as ΙΙmethy IpyrroUdone, dimethylacetamide and dimethylformamide 10 can likewise be employed. * Organic bases are preferably employed as bases to adjust the alkaline pH, for example basic amino acids, such as L- or D,L-arg1n1ne, L- or D,L-lysine, but also choline, methyIglucosamine, glucosamine and 2-am1no-215 hydroxymethy1-1,3-propanedlol. Diamines are also suitable for this purpose, for example, N,N,N',Na-tetrak1s(2hydroxypropy Dethy lenedlamlne or polyether tetrol based on ethylenediamine (N.W. 480-420, OH Index 432-467) Likewise forms clear solutions 1n the Indicated pH range.
Inorganic bases can also be employed, for example ammonia or sodium carbonate, where appropriate with the addition of water.
If substances and agents which are suitable for prophylaxis and/or medication are administered to the ani25 mats at the same time as agents for coccidla, they can additionally be incorporated in the formulation In order to function as the basic component 1n the formulation, for example aminoglycoside antibiotics, such as streptomycin, gentamicin, slsomlcln, eomlcln, or macrolide anti30 biotics, such as tylosin or kltasamydn, or sodium salts of sulphonamldes.
Substances which are otherwise used as emulsifiers or solubilisers and which are colloidally soluble In water can be employed In this case Like polar solvents as Long as a basic auxiliary 1s also added to them.
As has already been mentioned In the Introduction,that ( It is not possible by solubilisation without the addition of substances having alkaline effects to keep the active compound 1n solution at the final concentration for a pro longed period· However, such emulsifiers can be added to the abovementioned, claimed solutions in order, for example, to facilitate the distribution in water or to wet suspended auxiliaries. Polyoxyethylated substances are particularly suitable for this purpose, such as, for example, polyoxyethylated castor oil, polyethylene glycol10 sorbitan monooleate, polyethylene glycol-nonyIphenyI, poly ethylene glycol stearate or polyethylene glycol ethers. Basic derivatives, such as polyethylene glycoL-aLkylamines are particularly advantageous for this purpose.
Solutions or suspensions of the type described above can aLso contain 0.1 to 20X by weight, preferably 0.1-10X by weight, of other formulation auxiliaries, such as antioxidants, other surfactants, suspension stabilisers and thickening agents, such as, for example, methylcellulose, colloidal silica and others. The addition of a colorant, flavouring and builders to the animat feed is also possible. Moreover, acids which form a buffer system together with the initially Introduced base or which reduce the pH of the solution should be mentioned here.
The following examples are intended to outline the nature of the Invention without thereby restricting it.
To prepare the solutions according to the invention, the substances are weighed Into a container having a stirrer and then stirred, while heating, until a clear solution has been produced. In the examples listed/ the active compound is stable at 50°C for one month. If the solutions from the examples are diluted 1 : 1,000 with water, the pH of the water is in the range greater than 8 described above.
Exaaple 1 2.5 g of active conpound are dissolved to 100 al of trlethanolaalne by heating.
The clear solution has a pH of 10.2.
Exaaple 2 2.5 g of active conpound and 12.5 g of lactic acid are dissolved to 100 al In trlethanolaalne with heating and stirring.
The pH of the solution 1s 8.3.
Exaaple 3 .0 g of active conpound are dissolved to 100 al of aonoethanolaalne.
The clear solution has a pH of 11.
Exaaple 4 Active conpound 5.0 g Propylene glycol 50.0 g Sodiua carbonate 5.0 g Water ad 100 al pH of the solution 9.9.
Exaaple 5 .0 g of active conpound .0 g of DzL>Lys1ne base ad 100 nl with polyethylene glycol 400 pH of the solution 9.8.
Exanple 6 .0 g of active conpound 10.0 g of aonoethanolaalne ad 100 nl with N-aethyLpyrrolldone pH of the soLutlon 10.8.
Claims (17)
1. A water-miscible solution of l-CS-methyl-^tA 1 trifluoromethylthiophenoxy)phenyl]-3-methyl-l,3,5-triazin2,4,6(1H,3H,5H)-trione containing one or more polar solvents and which has an alkaline reaction.
2. A water-miscible solution according to Claim 1, wherein the pH is 8 to 11.
3. A water-miscible solution according to Claim 1, wherein the solvent employed is a polar solvent having an alkaline reaction.
4. A water-miscible solution according to Claim 3, wherein ethanolamine is employed as the solvent.
5. A water-miscible solution according to Claim 1, which contains, dissolved or suspended, a water-soluble substance having an alkaline reaction.
6. A water-miscible solution according to Claim 5, which contains a medicament as the water-soluble substance having an alkaline reaction.
7. A water-miscible solution according to Claim 1, which contains l-E3-methyl-4-(4 *-trifluoromethylthiophenoxy)phenyl]3-methyl-l,3,5-triazin-2,4,6(IH,3H,5H)trione in a concentration of 0.5-50% by weight.
8. A water-miscible solution according to Claim 7, which contains the active confound in a concentration of 1-25% by weight.
9. A water-miscible solution according to Claim 1, which contains 0.1-20% by weight of one or more additional formulation auxiliaries.
10. A water-miscible solution according to Claim 1, which is adjusted by an additive having an alkaline reaction such that, after dilution with water to the concentration for administration, it has a pH of 8 to 11.
11. Use of a water-miscible solution according to Claim 1 for controlling coccidiosis illnesses in animals.
12. - Use of a Woter-miscible solution according to Claim 1 for controlling coccidia illnesses and illnesses of animals, especially of poultry, which are induced by coccidia and similar pathogens. 5
13. Use of a water-miscible solution according to Claim S 1 as a concentrate for the preparation of ready-to-use 1 drinking water for animal breeding and production.
14. A process for the preparation of a water-miscible / solution according to Claim 1, which comprises dissolving 10 l-[3-methyl-4-(4'-trifluoromethylthiophenoxy)phenyl]-3methyl-1,3,5-triazin-2,4,6(ΙΗ,3H,5H)-trione in a polar, water-miscible solvent which optionally has an alkaline reaction, and adjusting the solution to a pH of 8 to 11 by, where appropriate, dissolving or suspending an alkaline 15. Governing additive.
15. A water-miscible solution according to Claim 1, substantially as hereinbefore described with particular reference to the accompanying Examples.
16. A process according to Claim 14 for the preparation
17. 20 of water-miscible solution, substantially as hereinbefore described, with particular reference to the accompanying Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833300793 DE3300793A1 (en) | 1983-01-12 | 1983-01-12 | Coccidiosis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE840047L IE840047L (en) | 1984-07-12 |
| IE56522B1 true IE56522B1 (en) | 1991-08-28 |
Family
ID=6188113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE47/84A IE56522B1 (en) | 1983-01-12 | 1984-01-11 | Agent for coccidiosis |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0116175B1 (en) |
| JP (1) | JPS59139316A (en) |
| KR (1) | KR900007310B1 (en) |
| AT (1) | ATE40792T1 (en) |
| AU (1) | AU561923B2 (en) |
| CS (1) | CS235997B2 (en) |
| DE (2) | DE3300793A1 (en) |
| DK (1) | DK165668C (en) |
| ES (1) | ES528805A0 (en) |
| FI (1) | FI81961C (en) |
| HU (1) | HU192529B (en) |
| IE (1) | IE56522B1 (en) |
| IL (1) | IL70641A (en) |
| MY (1) | MY101193A (en) |
| PH (1) | PH20973A (en) |
| PT (1) | PT77916B (en) |
| SU (1) | SU1276249A3 (en) |
| ZA (1) | ZA84219B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3408768A1 (en) * | 1984-03-09 | 1985-09-12 | Bayer Ag, 5090 Leverkusen | IMMUNTIMULATING AGENTS |
| DE3703105A1 (en) * | 1987-02-03 | 1988-08-11 | Bayer Ag | MEDICINE AGAINST PROTOCOES IN INSECTS |
| DE3703103A1 (en) * | 1987-02-03 | 1988-08-11 | Bayer Ag | AGENT AGAINST FISH PARSITES |
| DE3814323A1 (en) * | 1988-04-28 | 1989-11-09 | Hoechst Ag | WATER-SOLUBLE PREPARATIONS BY COCCIDIOSTATICA |
| CZ146296A3 (en) * | 1995-06-02 | 1997-04-16 | American Cyanamid Co | 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or thiotriones, process of their preparation and herbicidal agents |
| CA2294033C (en) * | 1997-07-29 | 2007-01-09 | Pharmacia & Upjohn Company | Pharmaceutical composition for acidic lipophilic compounds in a form of a self-emulsifying formulation |
| DE19824483A1 (en) | 1998-06-02 | 1999-12-09 | Bayer Ag | Semi-solid aqueous preparations for oral application of toltrazuril sulfone |
| DE102007025908A1 (en) | 2007-06-01 | 2008-12-04 | Bayer Healthcare Ag | Formulations containing triazinones and iron |
| DE102009012423A1 (en) | 2009-03-10 | 2010-09-16 | Bayer Animal Health Gmbh | Preparation based on oil |
| EP2740469A1 (en) | 2012-12-07 | 2014-06-11 | Ceva Sante Animale | New treatments with triazines |
| EP2740492A1 (en) | 2012-12-07 | 2014-06-11 | Ceva Sante Animale | Triazine formulations with a second active ingredient and surfactant(s) |
| EP2740470A1 (en) | 2012-12-07 | 2014-06-11 | Ceva Sante Animale | Treatment of Coccidiosis with intramuscular triazine composition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1476867A (en) * | 1966-03-04 | 1967-04-14 | Wellcome Found | Preparation of stable aqueous solutions containing a mixture of sulfaquinoxaline and diaveridine |
| DE2718799A1 (en) * | 1977-04-27 | 1978-11-09 | Bayer Ag | 1- (4-PHENOXY-PHENYL) -1,3,5-TRIAZINE DERIVATIVES, THE METHOD FOR THEIR MANUFACTURING AND THEIR USE AS A MEDICINAL PRODUCT AND GROWTH PROMOTER |
| CA1185974A (en) * | 1981-12-03 | 1985-04-23 | Adolf Parg | 1,3,5-triazinones and their use for controlling undesirable plant growth |
-
1983
- 1983-01-12 DE DE19833300793 patent/DE3300793A1/en not_active Withdrawn
- 1983-12-30 DE DE8383113224T patent/DE3379195D1/en not_active Expired
- 1983-12-30 AT AT83113224T patent/ATE40792T1/en not_active IP Right Cessation
- 1983-12-30 EP EP83113224A patent/EP0116175B1/en not_active Expired
-
1984
- 1984-01-03 PT PT77916A patent/PT77916B/en unknown
- 1984-01-09 CS CS84177A patent/CS235997B2/en unknown
- 1984-01-09 IL IL70641A patent/IL70641A/en not_active IP Right Cessation
- 1984-01-09 SU SU843688287A patent/SU1276249A3/en active
- 1984-01-09 PH PH30080A patent/PH20973A/en unknown
- 1984-01-10 AU AU23172/84A patent/AU561923B2/en not_active Expired
- 1984-01-10 FI FI840082A patent/FI81961C/en not_active IP Right Cessation
- 1984-01-11 IE IE47/84A patent/IE56522B1/en not_active IP Right Cessation
- 1984-01-11 HU HU8475A patent/HU192529B/en not_active IP Right Cessation
- 1984-01-11 JP JP59002127A patent/JPS59139316A/en active Granted
- 1984-01-11 DK DK012184A patent/DK165668C/en not_active IP Right Cessation
- 1984-01-11 ZA ZA84219A patent/ZA84219B/en unknown
- 1984-01-11 ES ES528805A patent/ES528805A0/en active Granted
- 1984-01-12 KR KR1019840000108A patent/KR900007310B1/en not_active IP Right Cessation
-
1987
- 1987-09-29 MY MYPI87002276A patent/MY101193A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2317284A (en) | 1984-07-19 |
| HU192529B (en) | 1987-06-29 |
| JPS59139316A (en) | 1984-08-10 |
| IE840047L (en) | 1984-07-12 |
| DE3379195D1 (en) | 1989-03-23 |
| AU561923B2 (en) | 1987-05-21 |
| FI840082A (en) | 1984-07-13 |
| CS235997B2 (en) | 1985-05-15 |
| PT77916B (en) | 1986-04-16 |
| ATE40792T1 (en) | 1989-03-15 |
| DK165668C (en) | 1993-06-01 |
| DK12184D0 (en) | 1984-01-11 |
| IL70641A0 (en) | 1984-04-30 |
| DK165668B (en) | 1993-01-04 |
| KR840007355A (en) | 1984-12-07 |
| JPH0216730B2 (en) | 1990-04-18 |
| PT77916A (en) | 1984-02-01 |
| FI81961C (en) | 1991-01-10 |
| DK12184A (en) | 1984-07-13 |
| FI840082A0 (en) | 1984-01-10 |
| EP0116175A3 (en) | 1986-02-19 |
| ES8500058A1 (en) | 1984-10-01 |
| ZA84219B (en) | 1984-09-26 |
| MY101193A (en) | 1991-07-31 |
| EP0116175A2 (en) | 1984-08-22 |
| KR900007310B1 (en) | 1990-10-08 |
| PH20973A (en) | 1987-06-15 |
| FI81961B (en) | 1990-09-28 |
| DE3300793A1 (en) | 1984-07-12 |
| SU1276249A3 (en) | 1986-12-07 |
| EP0116175B1 (en) | 1989-02-15 |
| ES528805A0 (en) | 1984-10-01 |
| IL70641A (en) | 1987-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |