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Compound in triazine class for anti activity of coccidian, preparation method and application

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 shortening the service life of anti-coccidial drugs, affecting exports, and failure of prevention and control.

Inactive Publication Date: 2007-10-10
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 continuous emergence of clinical drug-resistant strains, resulting in the emergence of coccidiostat resistance, resulting in shortened service life of anticoccidial drugs, control failure or poor effect, Cause clinical or subclinical coccidiosis in chickens, bring difficulties to the drug control of chicken coccidiosis, and seriously threaten the effect of drug control

Method used

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  • Compound in triazine class for anti activity of coccidian, preparation method and application
  • Compound in triazine class for anti activity of coccidian, preparation method and application
  • Compound in triazine class for anti activity of coccidian, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Synthesis of 2-[4-(4′-dichloroacetamidophenoxy)-3-methyl-phenyl]-1,2,4-triazine-3,5-dione

[0069] Step A: Synthesis of 2-methyl-4-nitro-4'-acetamido-diphenyl ether

[0070] Dissolve 12.6 g of potassium oxide particles in 250 ml of DMSO, and heat to 80° C. with stirring. 24g of acetaminophen was dissolved in 40ml of DMSO, and slowly added to the reaction solution. After the addition, the temperature was raised to reflux for 30 minutes, and 150 benzene was added to divide the water. 27.5 g of 2-chloro-5-nitrotoluene was dissolved in 80 ml of DMSO, then added dropwise to the above reaction solution, and reacted at room temperature for 10 hours. Afterwards, the reaction solution was poured into 2.5 L of water, stirred vigorously for 1 hour, the crude product was filtered out, washed with water until the filtrate was colorless, and dried. The crude product was recrystallized from ethanol / water to obtain 38.9 g of white solid with a yield of 86%. Melting point: 165.5-166...

Embodiment 2

[0082] Synthesis of 2-[4-(4′-dichloroacetamidophenoxy)-3,5-dichloro-phenyl]-1,2,4-triazine-3,5-dione

[0083] The operation steps are the same as in Example 1, and in step A, 3,4,5-trichloro-nitrobenzene is used as a reactant.

[0084] Melting point: 226.0~227.8℃;

[0085] ES-MS (m / z): 473.4 (M-H) - .

Embodiment 3

[0087] Synthesis of 2-[4-(4′-thiazolaminophenoxy)-3-methyl-5-chloro-phenyl]-1,2,4-triazine-3,5-dione

[0088] The operation steps are the same as in Example 1, and in step A, 2,3-dichloro-5-nitrotoluene is used as the reactant.

[0089] Step F: Dissolve 4.54 g of 2-[4-(4'-aminophenoxy)-3-methyl-5-chloro-phenyl]-1,2,4-triazine-3,5-dione Add 1ml of pyridine to 20ml of anhydrous DMF, add 2.3g of 2-bromothiazole dropwise at room temperature, drop it in 30 minutes, rise to 80°C for 4 hours, add 30ml of water, filter after cooling, dry, methanol / Recrystallized from water to obtain 2.6 g of a light yellow product with a yield of 62%.

[0090] Melting point: 252.3~254.5℃;

[0091] ES-MS (m / z): 427.4 (M-H) - .

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Abstract

This invention discloses novel triazine compounds with anti-coccidial activity, their preparation method and application. The general structural formula of the compounds is shown in formula 1, wherein, R1 and R2 are the same or not, and are selected from H, halogen, alkyl, alkoxy, nitro and trifluoromethyl; R3 is COR7, cycloalkyl, or heterocycle; R4 is H or alkyl. The acids for forming pharmaceutically acceptable salts of the compounds include HCl, H2SO4, HBr, H3PO4, H2CO3, formic acid, acetic acid, citric acid, lactic acid, fumaric acid, tartaric acid, and gluconic acid. The alkalis for forming pharmaceutically acceptable salts of the compounds include NaOH, KOH, triethylamine, and t-butylamine. The compounds have good inhibitive effects on animal coccidiosis.

Description

technical field [0001] The present invention relates to compound and its preparation and application, especially a novel triazine compound with anti-coccidial activity, preparation method and application thereof. 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 sulfonamides, polyether ionoph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/07A61K31/53A61P33/00
Inventor 薛飞群冯超张丽芳费陈忠郑文丽张可煜王霄旸
Owner SHANGHAI VETERINARY RES INST CHINESE ACAD OF AGRI SCI
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