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Pteridine compounds and application of same in pharmacy

A compound, pteridine technology, applied in the field of medicine, can solve the problems of narrow treatment window and affect the clinical treatment level, and achieve the effect of strong selectivity and broad application prospects.

Inactive Publication Date: 2019-10-22
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A major theoretical issue is that CDKs play a key role in the proliferation of normal cells as well as cancer cells, which may cause a narrow therapeutic window, and their toxicity will affect the level of clinical treatment

Method used

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  • Pteridine compounds and application of same in pharmacy
  • Pteridine compounds and application of same in pharmacy
  • Pteridine compounds and application of same in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Preparation of Compound I-1

[0039] (1) Intermediate compound 2-chloro-N 4 – Preparation of isopropylpyrimidine-4,5-diamine

[0040]

[0041] 5-Amino-2,4-dichloropyrimidine (25.0 g, 0.15 mol) was dissolved in anhydrous tetrahydrofuran (100 mL), and under stirring at room temperature, triethylamine was added dropwise to the reaction system using a constant pressure dropping funnel The mixed solution of (30.4g, 0.3mol) and isopropylamine (17.7g, 0.3mol) was dripped, and the reaction system was moved to an oil bath at 80° C. to react for 8h. TLC detected that the reaction was complete, and after cooling to room temperature, water (100 mL) was added, extracted with ethyl acetate (100 mL×3), and the organic phases were combined. The organic phase was washed with saturated sodium chloride water, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated and purified by silica gel column chromatography to obtain a reddish-brown soli...

Embodiment 2

[0051] Example 2 Preparation of Compound I-2

[0052]

[0053] With reference to Example 1, 4-(4-methylpiperazine)aniline in step (3) was replaced with equimolar amount of N,N-dimethyl-1,4-phenylenediamine, other conditions were unchanged, Compound I-2 was obtained (yield 72%).

[0054] MS-ESI(m / z): 340.2[M+H]+; 1 H NMR (400MHz, DMSO) δ: 12.57(s,1H), 8.86(s,1H), 7.32(s,1H), 7.00(d,2H), 6.76(d,2H), 3.80(q,1H) ,3.02(s,6H),1.26(d,6H)

Embodiment 3

[0055]Example 3 Preparation of Compound I-3

[0056] (1) Intermediate 2-chloro-N 4 – Preparation of tert-butylpyrimidine-4,5-diamine

[0057]

[0058] 5-Amino-2,4-dichloropyrimidine (0.15mol) was dissolved in anhydrous tetrahydrofuran (100mL), and under stirring at room temperature, triethylamine (30.4g) was added dropwise to the reaction system using a constant pressure dropping funnel. , 0.3mol) and tert-butylamine (21.9g, 0.3mol) mixed solution, after dripping, the reaction system was moved to 100 ℃ oil bath to react for 16h. TLC detected that the reaction was complete, and after cooling to room temperature, water (100 mL) was added, extracted with ethyl acetate (100 mL×3), and the organic phases were combined. The organic phase was washed with saturated sodium chloride water, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated and purified by silica gel column chromatography to obtain a reddish-brown solid (21.0 g, yield 69.8%). MS...

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PUM

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Abstract

The invention discloses pteridine compounds and application of the same in pharmacy, belonging to the field of medicine. The pteridine compounds of the invention or stereoisomers thereof or pharmaceutically acceptable salts thereof have a structure as shown in a general formula (I) or (II), have CDK4 inhibiting activity of 47% or more (as high as 79%), show very good inhibitory activity against CDK4 / 6, and can be used as highly-effective inhibitors againast CDK4 / 6, and have broad application prospects.

Description

technical field [0001] The invention relates to a pteridine compound and its application in pharmacy, and belongs to the field of medicine. Background technique [0002] Cancer is one of the major diseases affecting human health and has now become an important public health problem worldwide. According to data from the National Bureau of Statistics of my country in 2015, the incidence of malignant tumors in China accounts for about 21.8% of the global incidence of malignant tumors, and the overall level is at the upper middle level. The mortality rate of malignant tumors ranks first in the mortality rate of various diseases among Chinese residents, mainly including lung cancer, liver cancer, gastric cancer, esophagus cancer, colorectal cancer and breast cancer. It is a major disease that seriously threatens the public health of residents. Breast cancer has the highest incidence among female cancer patients. Every year, the number of female breast cancer cases in my country...

Claims

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Application Information

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IPC IPC(8): C07D475/00A61P35/00A61P35/02A61K31/519A23L33/10
CPCC07D475/00A61P35/00A61P35/02A23L33/10A23V2002/00A23V2200/308A23V2200/30
Inventor 唐春雷张晴胡小霞赵辉赵宽涛张月范为正
Owner JIANGNAN UNIV
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