CN101050202A - Compound in triazine class for anti activity of coccidian, preparation method and application - Google Patents

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

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CN101050202A
CN101050202A CN 200710040920 CN200710040920A CN101050202A CN 101050202 A CN101050202 A CN 101050202A CN 200710040920 CN200710040920 CN 200710040920 CN 200710040920 A CN200710040920 A CN 200710040920A CN 101050202 A CN101050202 A CN 101050202A
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compound
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薛飞群
冯超
张丽芳
费陈忠
郑文丽
张可煜
王霄旸
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Shanghai Veterinary Research Institute CAAS
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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

Novel compound in triazine class, preparation method and application thereof with coccidiostat activity
Technical field
The present invention relates to the preparation and the application of compound and compound, particularly a kind of novel compound in triazine class, preparation method and application thereof with coccidiostat activity.
Background technology
Coccidia be a kind ofly parasitize in bile duct and the intestinal epithelial cells, very wide protozoon distributes.Animals such as horse, ox, sheep, pig, camel, dog, rabbit, mink, chicken, turkey, duck, goose, dove can both suffer from coccidiosis, and the easy infection of chick, turkey wherein endangers the heavyliest, is one of most important disease in the intensification poultry husbandry.Because of immunization prevention and control coccidiosis of chicken still has many technology barriers and condition restriction, medicine is the topmost measure of this disease of control for a long time.Anticoccidial drug mainly contains several big classes such as sulfamido, polyethers ion carrier antibiotic, triazines.
But also there is defective in anticoccidial drug commonly used, and the ionophore medicine has being subjected to following or contacting or take in the toxicity hazard that is caused unintentionally of medicine animal and other farming animals and people, and drug safety is low, the drug effect narrow range.Polyether antibiotics Salinomycin. and Luo Luo mycin etc. can reduce the hatching rate of laying hen; The Robenidine life-time service has peculiar smell in the chicken.Be exactly residues of antibiotics in addition, the European Union and the U.S. require very strict to the antibiotic residual quantity in the animal-derived food product, if the microbiotic improper use will inevitably cause residual the exceeding standard in chicken and the egg and influence outlet.In addition, enter the nineties in 20th century, anticoccidial drug long-term and cause clinically that drug-resistant worm plant constantly occurs, cause the chemical sproof generation of coccidia, cause anticoccidial drug shortening working life, control failure or poor effect cause clinical or subclinical coccidiosis of chicken, bring a difficult problem, the effect of serious threat medical treatment for the medical treatment of coccidiosis of chicken.So probing into the anticoccidial drug of novel, efficient, low toxicity, safety has great importance.
Summary of the invention
The objective of the invention is a kind of novel compound in triazine class, preparation method and application thereof of designing at the deficiencies in the prior art with coccidiostat activity,
The object of the present invention is achieved like this:
A kind of novel compound in triazine class with coccidiostat activity, its structure are following general formula (I):
Figure A20071004092000081
Formula (I)
And the salt that is formed on pharmaceutically acceptable acid or alkali with this structural formula; In its formula (1):
R 1, R 2Represent one or more groups of hydrogen, halogen atom, alkyl, alkoxyl group, nitro, trifluoromethyl, R 1, R 2The group of representative can be the same or different.
R 3Represent COR 7, cycloalkyl, heterocycle.
R 4Represent hydrogen atom, alkyl.
R wherein 3, R 4Can with nitrogen-atoms Cheng Huan:
Figure A20071004092000082
R 5Represent hydrogen atom, alkyl.
R 6Represent hydrogen atom, CO 2R 4
R 7Represent 3-trifluoromethyl, 3,5-bis trifluoromethyl, CHCl 2, CHBr 2, OR 4, SR 4
-" halogen " is defined as fluorine, chlorine, bromine, iodine, astatine.
-" alkyl " is defined as C 1-C 6The saturated group of straight or branched.
The end that-" alkoxyl group " is defined as oxygen is connected with the group of alkyl.
-" cycloalkyl " is defined as C 1-C 6Cyclic group.
-" heterocycle " is defined as saturated or undersaturated single or two-cyclic group, have aromatics or non-aromatic character, have 5-12 annular atoms, contain 1-3 identical or different heteroatoms, heteroatoms is selected from oxygen, nitrogen and sulphur, heterocycle can randomly be replaced by one or more identical or different substituting groups, and substituting group is selected from halogen, hydroxyl, alkyl, alkoxyl group, nitro, pyridyl, thienyl, thiazolyl, furyl, imidazolyl, pyrazinyl, pyrimidyl, tetrazyl, pyrazolyl, quinolyl, isoquinolyl, quinazolyl, pyrrolidyl, pyridyl, piperazinyl, the dioxygen ethylene imine base, oxazolyl, purine radicals, different purine radicals.
All compounds and be formed on the salt of pharmaceutically acceptable acid or alkali.
The salt of pharmaceutically acceptable acid is meant salt crystal water or that do not contain crystal water that contains of hydrochloric acid, sulfuric acid, Hydrogen bromide, phosphoric acid, carbonic acid, formic acid, acetate, citric acid, lactic acid, fumaric acid, tartrate and gluconic acid formation.
The salt of pharmaceutically acceptable alkali is meant salt crystal water or that do not contain crystal water that contains that sodium hydroxide, potassium hydroxide, triethylamine, TERTIARY BUTYL AMINE forms.
According to a kind of favourable change example, preferred compound is: R wherein 3Be COR 7, cycloalkyl, heterocycle, halo acyl group, wherein R 7Define suc as formula (I).
According to the present invention, be for the preferred compound of formula (I):
R 1=methyl, methoxyl group; R 2=methyl, methoxyl group; R 3=dichloro-acetyl; R 4, R 5, R 6=hydrogen.
R 1=methyl, methoxyl group; R 2=hydrogen; R 3=dichloro-acetyl, two acetyl bromides; R 4, R 5, R 6=hydrogen.
R 1=methyl, methoxyl group; R 2=chlorine; R 3=dichloro-acetyl, two acetyl bromides; R 4, R 5, R 6=hydrogen.
R 1=chlorine; R 2=hydrogen; R 3=dichloro-acetyl, two acetyl bromides; R 4, R 5, R 6=hydrogen.
R 1=chlorine; R 2=chlorine; R 3=dichloro-acetyl, two acetyl bromides; R 4, R 5, R 6=hydrogen.
R 1=methyl, methoxyl group; R 2=hydrogen; R 3=dichloro-acetyl, two acetyl bromides; R 4=methyl; R 5=hydrogen.
R 1=methyl, methoxyl group; R 2=hydrogen; R 3=dichloro-acetyl, two acetyl bromides; R 4=methyl; R 5=methyl; R 6=hydrogen.
R 1=methyl, methoxyl group; R 2=hydrogen; R 3=dichloro-acetyl, two acetyl bromides; R 4=methyl; R 5=methyl; R 6=CO 2R 4R 4=hydrogen atom, alkyl.
R 1=methyl, methoxyl group; R 2=hydrogen; R 3=COR 7R 7=methoxyl group, methylthio group; R 4, R 5, R 6=hydrogen.
R 1=chlorine; R 2=chlorine; R 3=COR 7R 7=methoxyl group, methylthio group; R 4, R 5, R 6=hydrogen.
R 1=methyl, methoxyl group; R 2=hydrogen; R 3=COR 7R 7=methoxyl group, methylthio group; R 4=methyl; R 5, R 6=hydrogen.
R 1=methyl, methoxyl group; R 2=hydrogen; R 3=thiazolyl; R 4, R 5, R 6=hydrogen.
R 1=methyl, methoxyl group; R 2=hydrogen; R 3=3, the 5-bis trifluoromethyl; R 4, R 5, R 6=hydrogen.
These compounds and be formed on the salt of pharmaceutically acceptable acid or alkali.
Preferred compound and the salt that is formed on pharmaceutically acceptable acid or alkali are parts that constitutes complete content of the present invention.
According to the present invention,, it is characterized in that using the compound of formula (II) and the compound of formula (III) to be raw material for the preparation method of formula (I) compound:
Figure A20071004092000101
Formula (II) formula (III)
This preparation process comprises:
According to the Sa Mulete in the organic synthesis (Sandmeyer) reaction conditions, make the reaction of formula (II) compound obtain formula (IV) compound:
Figure A20071004092000111
Formula (IV)
R wherein 1, R 2Be as defined above.
According to the reaction of the metal of routine and acid reduction nitro, the reduction of formula (IV) compound obtains:
Figure A20071004092000112
Formula V
R wherein 1, R 2Be as defined above.
The coupling of formula V compound and formula (III) compound obtains formula (VI) compound:
Figure A20071004092000113
Formula (VI)
R wherein 1, R 2Be as defined above.
Add the closed loop agent in formula (VI) compound, obtain crucial intermediate formula (VII) through diazonium coupling, cyclization, hydrolysis decarboxylation reaction:
Figure A20071004092000114
Formula (VII)
R wherein 1, R 2, R 5, R 6Be as defined above.
Formula (VII) compound is production (I/a) compound under the effect of dichloroacetyl chloride, that is:
A specific examples of formula (I) compound:
Figure A20071004092000121
Formula (I/a)
R wherein 1, R 2, R 5, R 6Be as defined above.
The compounds of this invention has tangible anti-animal coccidia activity.Contain the formed salt at pharmaceutical acceptable acid or alkali of at least a formula (I) compound or these compounds as activeconstituents, therefore can be used for the prevention of animal's coccidiosis.
Embodiment
The following example is used for further specifying the present invention and limits the present invention absolutely not.
Raw materials used and or reagent be known product, or according to the product of known operation preparation.
The structure of compound described in embodiment and the synthesis step be according to routine spectroscopic techniques (infrared, UV, NMR MS) measures.
Embodiment 1
Synthetic 2-[4-(4 '-the acetamide chlcride phenoxyl)-3-methyl-phenyl]-1,2,4-triazine-3,5-diketone
Steps A: 2-methyl-4-nitro-4 '-acetylaminohydroxyphenylarsonic acid phenyl ether synthetic
Potassium oxide particle 12.6g is dissolved among the 250ml DMSO, is heated to 80 ℃ under stirring.Paracetamol 24g is dissolved among the 40ml DMSO, slowly joins in the reaction solution.Finish, temperature rising reflux 30 minutes adds 150 benzene and divides water.27.5g is dissolved among the 80ml DMSO with 2-chloro-5-nitrotoluene, is added drop-wise in the above-mentioned reaction solution room temperature reaction 10 hours then.Afterwards, reaction solution is poured in the 2.5L water, vigorous stirring 1 hour filters out crude product, and it is colourless to be washed to filtrate, drying.Crude product ethanol/water recrystallization obtains white solid 38.9g, yield 86%.Fusing point: 165.5～166.4 ℃.
Step B:4-amino-2-methyl-4 '-acetylaminohydroxyphenylarsonic acid phenyl ether synthetic
With 10.5g ferric sulfate, add 200ml water in the 11.2g reduced iron powder, stir heating in water bath to 60 ℃.With 14.3g 2-methyl-4-nitro-4 '-the acetylaminohydroxyphenylarsonic acid phenyl ether, be dissolved in the 700ml methylene dichloride, be added drop-wise in the reaction solution.React after 5 hours, cooling leaches iron mud, the phase of anhydrating filtrate branch, and organic phase washing three times, the anhydrous sodium sulfate drying after-filtration, pressurization is steamed and is removed 2/3 solvent, leaches faint yellow solid after the cooling, and drying obtains white cotton-shaped product 12.4g, yield 97%.Fusing point: 176.0～177.5 ℃.
Step C:2-[3-methyl-4-(4 '-kharophen phenoxy group) phenyl]-6-ethanoylaminoethanoic acid ethyl ester-1,2,4-triazine-3,5-diketone synthetic
With 10g 4-amino-2-methyl-4 '-the acetylaminohydroxyphenylarsonic acid phenyl ether is dissolved in 115ml water and the 20ml hydrochloric acid, stir, ice bath is cooled to 5 ℃, drip the aqueous solution of 3.17g Sodium Nitrite, temperature remains on below 5 ℃, drips off in 30 minutes, insulation reaction is 2 hours afterwards, add 8.2g Glacial acetic acid potassium and 11.1g malonyl-diamino acid ethyl ester then in batches, room temperature reaction 1 hour, temperature rising reflux is 2 hours again.Cooling adds 200ml water, filters, and drying obtains orange solid 19.0g, directly carries out next step reaction.
Step D:2-[3-methyl-4-(4 '-amino-benzene oxygen) phenyl]-6-carboxyl-1,2,4-triazine-3,5-diketone synthetic
To go up the step product and add 100ml acetate, the 50ml vitriol oil and 30ml water stir, and 3 hours postcooling of temperature rising reflux add 100ml water, leach faint yellow solid, washing, and drying obtains off-white color product 14.8g behind the DMF/ ethyl alcohol recrystallization, two step yields 82%.Fusing point: 256.0～258.6 ℃.
Step e: 2-[4-(4 '-amino-benzene oxygen)-3-methyl-phenyl]-1,2,4-triazine-3,5-diketone synthetic
To go up step product and 40ml Thiovanic acid and join in the reaction flask, nitrogen protection, magnetic agitation is warming up to 140 ℃; reacted 3 hours, cooling adds 20ml methyl alcohol and 20ml water, separates out solid; filter, drying obtains faint yellow product 9.3g, yield 72% behind the ethanol/water recrystallization.Fusing point: 239.0～242.5 ℃.
Step F: 2-[4-(4 '-acetamide chlcride phenoxyl)-3-methyl-phenyl]-1,2,4-triazine-3,5-diketone synthetic
Product 3.1g of last step is dissolved into 15ml not to be had among the DMF of water treatment, adds the 1ml pyridine, and ice bath is cooled to 0 ℃, beginning slowly drips the 2.0ml dichloroacetyl chloride, dripped off in 20 minutes, and kept reaction below 5 ℃ 30 minutes, rose to room temperature reaction again 2 hours, add 30ml water, separate out solid, filter, wash, use the ethanol/water recrystallization, obtain faint yellow solid 3.6g, yield 87%.Fusing point: 202.5～204.5 ℃.ES-MS(m/z)：419.2(M-H) -。
Embodiment 2
Synthetic 2-[4-(4 '-the acetamide chlcride phenoxyl)-3,5-two chloro-phenyl]-1,2,4-triazine-3,5-diketone
Operation steps uses 3,4 with embodiment 1 in steps A, 5-three chloro-oil of mirbane are as reactant.
Fusing point: 226.0～227.8 ℃;
ES-MS(m/z)：473.4(M-H) -。
Embodiment 3
Synthetic 2-[4-(4 '-the thiazole amino-benzene oxygen)-3-methyl-5-chloro-phenyl]-1,2,4-triazine-3,5-diketone
Operation steps uses 2 with embodiment 1 in steps A, 3-two chloro-5-nitrotoluenes are reactant.
Step F: with 4.54g 2-[4-(4 '-amino-benzene oxygen)-3-methyl-5-chloro-phenyl]-1,2,4-triazine-3, the 5-diketone is dissolved into 20ml not to be had among the DMF of water treatment, adds the 1ml pyridine, and room temperature drips the 2-bromo thiazole of 2.3g, dripped off in 30 minutes, rise to 80 ℃ of reactions 4 hours, add 30ml water, cooled and filtered, dry, the methanol recrystallization obtains light yellow product 2.6g, yield 62%.
Fusing point: 252.3～254.5 ℃;
ES-MS(m/z)：427.4(M-H) -。
Embodiment 4
Synthetic 2-[4-(4 '-along the rare imide phenoxyl of fourth)-3-methyl-phenyl]-1,2,4-triazine-3,5-diketone
Operation steps is with embodiment 1.
Step F: will go up step product 3.1g and be dissolved into 15ml and do not have among the DMF of water treatment, add the 1ml pyridine, 1.2g MALEIC ANHYDRIDE be dissolved into 6ml and do not have among the DMF of water treatment, room temperature drips, and drips off in 30 minutes, rise to 65 ℃ of reactions 6 hours, add 30ml water, cooled and filtered, drying, behind the Virahol recrystallization to product 2.5g, yield 60%.
Fusing point: 210.0～212.6 ℃;
ES-MS(m/z)：424.8(M-H) -。
Embodiment 5
Synthetic 2-[4-(4 '-the p-chlorobenzamido phenoxy group)-3,5-two chloro-phenyl]-1,2,4-triazine-3,5-diketone
Operation steps uses parachlorobenzoyl chloride as reactant in step F with embodiment 2.
Fusing point: 196.3～199.0 ℃;
ES-MS(m/z)：482.2(M-H) -。
Embodiment 6
Synthetic 2-[4-(4 '-dichloro acetamino-4 '-methyl-phenoxy group)-3-methyl-phenyl]-1,2,4-triazine-3,5-diketone
Operation steps is with embodiment 1
Step G: with the 2-[4-of 2.3g (4 '-acetamide chlcride phenoxyl)-3-methyl-phenyl]-1,2,4-triazine-3, the 5-diketone is dissolved in 10 dry DMF, adds the 1ml triethylamine, is cooled to 5 ℃, drip the methyl iodide of 0.9g, dripped off in 15 minutes, and rose to room temperature reaction and spend the night, add 15ml water, filter, drying, behind the ethyl alcohol recrystallization to product 1.7g, yield 72%.
Fusing point: 182.8～184.0 ℃;
ES-MS(m/z)：486.2(M-H) -。

Claims (10)

1, a kind of novel compound in triazine class with coccidiostat activity is characterized in that: structure is following general formula (I):
Figure A2007100409200002C1
Formula (I)
And the salt that is formed on pharmaceutically acceptable acid or alkali with this structural formula; In its formula (1):
R 1, R 2Represent one or more groups of hydrogen, halogen atom, alkyl, alkoxyl group, nitro, trifluoromethyl, R 1, R 2The group of representative is identical or different;
R 3Represent COR 7, cycloalkyl, heterocycle;
R 4Represent hydrogen atom, alkyl;
R wherein 3, R 4Can with nitrogen-atoms Cheng Huan:
Figure A2007100409200002C2
R 5Represent hydrogen atom, alkyl;
R 6Represent hydrogen atom, CO 2R 4
R 7Represent 3-trifluoromethyl, 3,5-bis trifluoromethyl, CHCl 2, CHBr 2, OR 4, SR 4
-" halogen atom " is fluorine, chlorine, bromine, iodine, astatine;
-" alkyl " is C 1-C 6The saturated group of straight or branched;
-" alkoxyl group " is connected with the group of alkyl for the end of oxygen;
-" cycloalkyl " is C 1-C 6Cyclic group;
-" heterocycle " is saturated or undersaturated single or two-cyclic group, have aromatics or non-aromatic character, have 5-12 annular atoms, contain 1-3 identical or different heteroatoms, heteroatoms is selected from oxygen, nitrogen and sulphur, heterocycle can randomly be replaced by one or more identical or different substituting groups, and substituting group is selected from halogen, hydroxyl, alkyl, alkoxyl group, nitro, pyridyl, thienyl, thiazolyl, furyl, imidazolyl, pyrazinyl, pyrimidyl, tetrazyl, pyrazolyl, quinolyl, isoquinolyl, quinazolyl, pyrrolidyl, pyridyl, piperazinyl, the dioxygen ethylene imine base, oxazolyl, purine radicals, different purine radicals;
The salt of described pharmaceutically acceptable acid is meant salt crystal water or that do not contain crystal water that contains of hydrochloric acid, sulfuric acid, Hydrogen bromide, phosphoric acid, carbonic acid, formic acid, acetate, citric acid, lactic acid, fumaric acid, tartrate and gluconic acid formation;
The salt of described pharmaceutically acceptable alkali is meant salt crystal water or that do not contain crystal water that contains that sodium hydroxide, potassium hydroxide, triethylamine, TERTIARY BUTYL AMINE forms.
2, according to formula (I) compound of claim 1, it is characterized in that it is R 1=methyl, methoxyl group; R 2=methyl, methoxyl group, hydrogen; R 3=dichloro-acetyl, two acetyl bromides; R4, R5, R6=hydrogen; The formed salt of these compounds and these compounds at pharmaceutically acceptable acid or alkali.
3, according to formula (I) compound of claim 1, it is characterized in that it is R 1=chlorine, bromine; R 2=chlorine, bromine; R 3=dichloro-acetyl, two acetyl bromides; R 4, R 5, R 6=hydrogen; The formed salt of these compounds and these compounds at pharmaceutically acceptable acid or alkali.
4, according to formula (I) compound of claim 1, it is characterized in that it is R 1=chlorine, bromine; R 2=chlorine, bromine; R 3=dichloro-acetyl, two acetyl bromides; R 4=methyl; R 5=methyl; R 6=CO 2R 4R 4=hydrogen atom, alkyl; The formed salt of these compounds and these compounds at pharmaceutically acceptable acid or alkali.
5, according to formula (I) compound of claim 1, it is characterized in that it is R 1=methyl, methoxyl group; R 2=chlorine, bromine; R 3=COR 7R 7=methoxyl group, methylthio group; R 4, R 5, R 6=hydrogen; The formed salt of these compounds and these compounds at pharmaceutically acceptable acid or alkali.
6, according to formula (I) compound of claim 1, it is characterized in that it is R 1=chlorine; R 2=chlorine; R 3=COR 7R 7=methoxyl group, methylthio group; R 4, R 5, R 6=hydrogen; The formed salt of these compounds and these compounds at pharmaceutically acceptable acid or alkali.
7, according to formula (I) compound of claim 1, it is characterized in that it is R 1=methyl, methoxyl group; R 2=hydrogen; R 3=thiazolyl; R 4, R 5, R 6=hydrogen; The formed salt of these compounds and these compounds at pharmaceutically acceptable acid or alkali.
8, according to formula (I) compound of claim 1, it is characterized in that it is R 1=methyl, methoxyl group; R 2=hydrogen; R 3=3-trifluoromethyl; R 4, R 5, R 6=hydrogen; The formed salt of these compounds and these compounds at pharmaceutically acceptable acid or alkali.
9, the preparation method of formula (I) compound is characterized in that using the compound of formula (II) and the compound of formula (III) to be raw material:
Figure A2007100409200004C1
Formula (II) formula (III)
R wherein 1, R 2Be as defined above;
By the reaction conditions of the reaction of the Sa Mulete in the organic synthesis, make the reaction of formula (II) compound obtain formula (IV) compound:
Figure A2007100409200005C1
Formula (IV)
R wherein 1, R 2Be as defined above;
The reaction of metal routinely and acid reduction nitro, the reduction of formula (IV) compound obtains:
Figure A2007100409200005C2
Formula V
R wherein 1, R 2Be as defined above;
The coupling of formula V compound and formula (III) compound obtains formula (VI) compound:
Figure A2007100409200005C3
Formula (VI)
R wherein 1, R 2Be as defined above;
Add the closed loop agent in formula (VI) compound, obtain intermediate formula (VII) through diazonium coupling, cyclization, hydrolysis decarboxylation reaction:
Formula (VII)
R wherein 1, R 2, R 5, R 6Be as defined above;
Formula (VII) compound is production (I/a) compound under the effect of dichloroacetyl chloride, that is: a specific examples of formula (I) compound:
Figure A2007100409200006C1
Formula (I/a)
R wherein 1, R 2, R 5, R 6Be as defined above.
10, formula (I) application of compound is characterized in that the application of this compound on anti-animal coccidia medicine.
CN 200710040920 2007-05-18 2007-05-18 Compound in triazine class for anti activity of coccidian, preparation method and application Pending CN101050202A (en)

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CN102285930A (en) * 2011-08-12 2011-12-21 中国农业科学院上海兽医研究所 Triazine compound and application thereof to chicken coccidiosis disease control
CN102408413A (en) * 2010-09-25 2012-04-11 中牧实业股份有限公司 Anticoccidial compound, and preparation method and use thereof
CN103554046A (en) * 2013-11-08 2014-02-05 中国农业科学院上海兽医研究所 Chicken coccidiosis preventing triazine compound
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CN102408413B (en) * 2010-09-25 2013-08-14 中牧实业股份有限公司 Anticoccidial compound, and preparation method and use thereof
CN102285930A (en) * 2011-08-12 2011-12-21 中国农业科学院上海兽医研究所 Triazine compound and application thereof to chicken coccidiosis disease control
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WO2015067193A1 (en) * 2013-11-08 2015-05-14 中国农业科学院上海兽医研究所 Triazine compound for combating coccidiosis in chickens
CN103554046A (en) * 2013-11-08 2014-02-05 中国农业科学院上海兽医研究所 Chicken coccidiosis preventing triazine compound
JP2016515547A (en) * 2013-11-08 2016-05-30 シャンハイ ベトリナリー リサーチ インスティチュート、チャイニーズ アカデミー オブ アグリカルチュラル サイエンシズＳｈａｎｇｈａｉ Ｖｅｔｅｒｉｎａｒｙ Ｒｅｓｅａｒｃｈ Ｉｎｓｔｉｔｕｔｅ，Ｃｈｉｎｅｓｅ Ａｃａｄｅｍｙ Ｏｆ Ａｇｒｉｃｕｌｔｕｒａｌ Ｓｃｉｅｎｃｅｓ Triazine compounds with anti-chicken coccidiosis
GB2528793B (en) * 2013-11-08 2019-10-09 Shanghai Veterinary Res Institute Triazine compound for combating coccidiosis in chickens
CN104610182A (en) * 2015-02-09 2015-05-13 中国农业科学院上海兽医研究所 Amorphous matter of triazine compound and preparation method and use thereof
CN104610183A (en) * 2015-02-09 2015-05-13 中国农业科学院上海兽医研究所 Triazine compound crystal form A and preparation method and application thereof
CN104610182B (en) * 2015-02-09 2017-03-15 中国农业科学院上海兽医研究所 A kind of amorphous substance of triaizine compounds and its production and use
CN111018801A (en) * 2019-12-25 2020-04-17 山东国邦药业有限公司 Preparation method of anticoccidial veterinary drug cimetiril

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