Triazine compounds having coccidiostat activity and preparation thereof

A compound, anti-coccidial technology, applied in the direction of active ingredients of heterocyclic compounds, organic chemistry, anti-infective drugs, etc., can solve the problems of antibiotic residues, excessive chicken and egg residues, toxicity hazards, etc.

Inactive Publication Date: 2009-04-15
SHANGHAI VETERINARY RES INST CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, commonly used anticoccidial drugs also have defects. Ionophore drugs have toxicity hazards caused by accompanying or unintentional contact or ingestion of drug-receiving animals and other farm animals and humans, and the drug safety is low and the range of drug effects is narrow.
Polyether antibiotics such as salinomycin and loromycin will reduce the hatchability of laying hens; long-term use of prophenylguanidine will cause peculiar smell in chicken
There is also the residue of antibiotics. The European Union and the United States have very strict requirements on the amount of antibiotic residues in animal food. If antibiotics are used improperly, the residues in chicken and eggs will inevitably lead to excessive residues and affect exports.
In addition, in the 1990s, the long-term use of anticoccidial drugs led to the emergence of drug-resistant strains in clinical practice, resulting in the emergence of drug resistance in coccidiostats, resulting in shortened service life of anticoccidial drugs, control failure or poor effect , causing clinical or subclinical chicken coccidiosis, bringing difficulties to the drug control of chicken coccidiosis or abuse diseases, and seriously threatening the effect of drug control

Method used

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  • Triazine compounds having coccidiostat activity and preparation thereof
  • Triazine compounds having coccidiostat activity and preparation thereof
  • Triazine compounds having coccidiostat activity and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Synthesis of 2-[4-(4'-trifluoromethylphenoxy)phenyl]-[1,2,4]-triazine-3,5-(2H,4H)-dione

[0062] Add 22.0g of p-hydroxyaniline, 25ml of water and 100ml of concentrated hydrochloric acid into the reaction flask, stir, cool down, add dropwise an aqueous solution containing 30.0g of sodium nitrite at 15~20°C, drop it in 30 minutes, keep it warm for 2 hours, and obtain the diazonium salt ,stand-by. Add 60.0g of ethyl malonyl dicarbamate, 300ml of pyridine, 300g of crushed ice and 200ml of water into another reaction flask. After cooling to below 10°C, pour the above diazonium salt slowly under vigorous stirring. After addition, react at 10~15°C for 5h. Filter and wash with water until neutral to obtain 70.3 g of ethyl 2-(4-hydroxyphenylhydrazone)-malonyl dicarbamate, with a yield of 95.1%.

[0063] Add 33.2g of 2-(4-hydroxyphenylhydrazone)-malonyldicarbamate, 20g of anhydrous sodium acetate and 250ml of glacial acetic acid into the reaction flask, heat and reflux for 5 ho...

Embodiment 2

[0068] 2-[4-(4'-trifluoromethylphenoxy)phenyl]-4-methyl-[1,2,4]-triazine-3,5-(2H,4H)-dione synthesis

[0069] 0.73g 2-[4-(4'-trifluoromethylphenoxy)phenyl]-[1,2,4]-triazine-3,5-(2H,4H)-dione, 0.1g Add sodium hydroxide and 20ml dimethyl sulfoxide into the reaction flask, stir at room temperature for 0.5h, add dropwise a mixed solution of 0.83g methyl iodide and 10ml dimethyl sulfoxide, and raise the temperature to 100°C after dropping, react for 5h, and the reaction is complete , down to room temperature, add about 100ml of water under stirring, filter, wash with water, and dry to obtain 0.67g of product with a yield of 88.5%.

Embodiment 3

[0071] Synthesis of 2-[4-(4'-nitrophenoxy)phenyl]-[1,2,4]-triazine-3,5-(2H,4H)-dione

[0072] Add 1.0 g of 2-(4-hydroxyphenyl)-[1,2,4]-triazine-3,5-(2H,4H)-dione, 0.75 g of anhydrous potassium carbonate and 40 ml of DMSO to the reaction flask , heated to 80°C and reacted for 30min with stirring, dissolved 0.8g p-nitrochlorobenzene in 10ml DMSO, added dropwise to the reaction flask, raised the temperature to 150°C and reacted for 10h, cooled down, added water (300ml), and adjusted the pH to 4 with dilute hydrochloric acid , filtered, washed with water, and dried to obtain 1.5 g of off-white powder product with a yield of 90.2%.

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PUM

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Abstract

The invention discloses triazine compounds of formula (I) which have anti-coccidia activity and the pharmaceutically acceptable acid or alkali salts of the compounds, wherein, A stands for oxygen or sulfur, R1 and R2 stand for one or several groups of hydrogen, halogen atoms, alkyl, naphthene base, alkoxy, nitryl, trifluoromethyl, trichloromethyl, COR5, naphthene base and heterocyclic rings; R1 and R2 stand for same or different groups; R3 stands for hydrogen atoms, alkyl or naphthene base; R4 stands for hydrogen atoms, CO2R5 or CONHR6; and the compounds have good inhabitation effect for animal coccidiosis.

Description

technical field [0001] The invention relates to a new triazine compound and its pharmaceutically acceptable acid or alkali salt; the invention relates to a preparation method of the new compound; and the compound has anti-coccidian activity. Background technique [0002] Coccidia are protozoa that parasitize in the bile duct and intestinal epithelial cells and are widely distributed. Animals such as horses, cattle, sheep, pigs, camels, dogs, rabbits, minks, chickens, turkeys, ducks, geese, and pigeons can all suffer from coccidiosis, among which young chickens and turkeys are the most susceptible to infection and the most harmful. One of the most important diseases in poultry farming. Because there are still many technical barriers and conditional restrictions in the prevention and control of chicken coccidiosis by immunization, medicine has been the most important measure for the prevention and treatment of the disease for a long time. Anticoccidial drugs mainly include s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/075A61K31/53A61P33/00
Inventor 薛飞群杨红伟张丽芳费陈忠郑文丽张可煜王霄旸裘敏琪
Owner SHANGHAI VETERINARY RES INST CHINESE ACAD OF AGRI SCI
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