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Quinazoline derivatives and their preparation and use

A technology of derivatives and drugs, applied in the field of medicine, to achieve a good effect of preventing and controlling chicken coccidiosis

Active Publication Date: 2021-12-24
LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, the research on chicken coccidiosis immune prevention has made some progress, but there are still some problems in its popularization and application

Method used

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  • Quinazoline derivatives and their preparation and use
  • Quinazoline derivatives and their preparation and use
  • Quinazoline derivatives and their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Preparation of 4-(3'-pyrrolidinylmethyl-4'-hydroxyanilino)quinazoline (compound Ia)

[0040] Step 1) Synthesis of 4-(p-hydroxyanilino) quinazoline (compound V)

[0041] Add 4-chloroquinazoline III (3.3g, 20.05mmol) and p-aminophenol IV (2.2g, 20.05mmol) into a 250mL three-necked flask, add ethyl acetate (100mL), heat to reflux at 78°C, and react 8h, TLC monitors the reaction, the developer is petroleum ether-ethyl acetate (volume ratio 1:2, 5 drops of methanol is added to every 1mL of ethyl acetate), almost complete. After the reaction was completed and the temperature was lowered to room temperature, suction filtration was performed, and the filter cake was rinsed with a small amount of ethyl acetate. Then put the filter cake into a 250 mL beaker, add 100 mL of saturated sodium bicarbonate solution, stir for 20 min, filter with suction, wash the filter cake with water until neutral, and dry naturally to obtain 3.8 g of off-white pure product with a yield of ...

Embodiment 2

[0046] Example 2 Preparation of 4-(3'-diethylaminomethyl-4'-hydroxyanilino)quinazoline (compound Ib)

[0047] According to the method in Example 1, this example uses intermediate V (when preparing, the reaction condition is 78 ° C under heating and reflux, the reaction time is 8 hours, and the rest of the preparation process is the same as in Example 1) as raw material, and formaldehyde and diethylamine are produced. Compound Ib was obtained by Nisch reaction (the reaction condition was reflux at 78°C, and the reaction time was 36h). The yield was 46.6%.

[0048] The structural confirmation data are as follows:

[0049] Melting point 195°C; 1 HNMR (600MHz, DMSO-d 6)δ9.62(s,1H),8.51–8.46(m,2H),7.82(ddd, J=8.3,6.9,1.3Hz,1H),7.74(dd,J=8.3,1.2Hz,1H),7.59 (ddd, J=8.2,6.8,1.3Hz,1H),7.50(dd,J=8.6,2.6Hz,1H),7.44(d,J=2.6Hz,1H),6.73(d,J=8.6Hz, 1H), 3.75(s, 2H), 2.58(q, J=7.1Hz, 4H), 1.05(t, J=7.1Hz, 6H).

Embodiment 3

[0050] Example 3 Preparation of 4-(3'-hexahydropyridylmethyl-4'-hydroxyanilino)quinazoline (compound Ic)

[0051] According to the method in Example 1, this example uses intermediate V (when preparing, the reaction condition is 75 ℃ heating to reflux, the reaction time is 10h, and the rest of the preparation process is the same as Example 1) as raw material, and formaldehyde, hexahydropyridine Compound Ic was obtained by Mannich reaction (the reaction condition was reflux at 75°C, and the reaction time was 35h). The yield was 72.7%.

[0052] The structural confirmation data are as follows:

[0053] Melting point 226°C; 1 HNMR (600MHz, DMSO-d 6 )δ10.87(s,1H),9.62(s,1H),8.49(d,J=2.7Hz,1H),8.48(d,J=1.3Hz,1H),7.81(ddd,J=8.3,6.9 ,1.3Hz,1H),7.74(dd,J=8.4,1.2Hz,1H),7.58(ddd,J=8.3,6.8,1.3Hz,1H),7.51(dd,J=8.6,2.6Hz,1H) ,7.42(d,J=2.6Hz,1H), 6.75(d,J=8.6Hz,1H),3.63(s,2H),2.46(s,4H),1.54(p,J=5.6Hz,4H) ,1.43(d,J=7.6Hz, 2H).

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Abstract

The invention discloses a new class of 4-(3'-R substituted-5'-R substituted-4'-hydroxyanilino) quinazoline derivatives, a preparation method and an application thereof. The structural formulas of the compounds are shown in formulas I and II. The compound of the invention has good activity of preventing and treating chicken coccidiosis, and can be used as a therapeutic agent for preventing and treating chicken coccidiosis in the field of preparation of medicines for preventing and treating chicken coccidiosis.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to the technical field of preparing medicines for preventing and treating chicken coccidiosis, specifically a 4-(3'-R substituted-5'-R substituted-4'-hydroxyanilino)quinazole A morphine compound used to prevent and treat coccidiosis in chickens, a preparation method and application thereof. Background technique [0002] Chicken coccidiosis is a parasitic protozoan disease caused by a variety of coccidia of the genus Eimeria parasitizing in the intestinal epithelial cells of chickens. Chicken coccidia are widely distributed and harmful. The morbidity and lethality of 10-30 day-old chicks or 35-60-day-old young chickens can be as high as 80%. The growth of the sick chicks is hindered, and the weight gain is slow; the adult chickens generally do not get sick, but they are carriers, and the weight gain and egg production ability are reduced, which is an important source of spreading c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/94C07D401/12C07D401/14A61P33/02A61K31/5377A61K31/517
CPCC07D239/94C07D401/12C07D401/14A61P33/02
Inventor 苗小楼尚小飞潘虎李冰张继瑜王瑜
Owner LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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