A kind of PDE2 inhibitor phenylpyrazolopyrimidine compound and preparation method thereof

A technology of phenylpyrazolopyrimidine and compound, applied in the field of medicinal chemistry, can solve the problem of low bioavailability in vivo, achieve excellent pharmacodynamic performance, good PDE2 inhibitory activity, and meet the requirements of industrialization

Active Publication Date: 2021-12-03
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The problem to be solved by the present invention: In order to overcome the deficiencies of existing inhibitors and the low bioavailability in vivo, and develop PDE2 inhibitors to meet the needs of social drug use, the present invention provides a PDE2 inhibitor phenylpyrazolopyrimidine Compounds and preparation methods thereof, the compounds have the advantages of good pharmacodynamic performance, simple structure, etc.

Method used

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  • A kind of PDE2 inhibitor phenylpyrazolopyrimidine compound and preparation method thereof
  • A kind of PDE2 inhibitor phenylpyrazolopyrimidine compound and preparation method thereof
  • A kind of PDE2 inhibitor phenylpyrazolopyrimidine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the preparation method of compound a

[0031] (1) Synthesis of 7-oxo-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid

[0032]

[0033] Weigh 1.2 g of beige solid powder 7-oxo-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate 1.2 g into a 250 mL round bottom flask, first Add 32 mL of EtOH, and the temperature is 20°C. After stirring for 5 min, add 16 mL of THF, and then slowly add 40 mL of water. After the temperature rose to 45°C, 570 mg of KOH was added, and the solid was almost completely dissolved after stirring for 10 min. Maintain the temperature at 50°C for the reaction. After 3 hours, 350 mg of KOH was weighed again and added to the reaction solution, and the temperature was raised to 80° C., at which point the solution was basically clear. After 3 hours, weigh 200 mg of KOH and add to the reaction system, reflux, stop the reaction for 12 hours, the solution is light pink, cool to room temperature, slowly add 1mol / L H...

Embodiment 2

[0037] Embodiment 2: the preparation method of compound b

[0038] Except that benzylamine was used instead of phenethylamine, the rest of the synthesis steps were the same as the synthesis method of compound a in Example 1. Synthesis of N-Benzyl-7-oxo-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide

[0039]

[0040] The purity detected by HPLC was 98.12%, and the yield was 49.4%. 1H NMR(400MHz,DMSO-d6)δ9.08(s,1H),8.01(s,1H),7.91–7.82(m,2H),7.39–7.32(m,8H),6.10(s,1H), 4.56(s,2H).

Embodiment 3

[0041] Embodiment 3: the preparation method of compound c

[0042] Except that n-butylamine was used instead of phenethylamine, the rest of the synthesis steps were the same as the synthesis method of compound a in Example 1. Synthesis of N-butyl-7-oxo-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide

[0043]

[0044] The purity detected by HPLC was 97.62%, and the yield was 54.8%. 1 HNMR(400MHz,DMSO-d6)δ8.70(s,1H),7.98(d,J=7.4Hz,2H),7.93(s,1H),7.52–7.34(m,3H),6.07(s,1H ), 3.32 (t, J = 10.0Hz, 2H), 1.59–1.49 (m, 2H), 1.43–1.40 (m, 2H), 0.93 (t, J = 7.2Hz, 3H).

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Abstract

The invention discloses a PDE2 inhibitor phenylpyrazolopyrimidine compound and a preparation method thereof, belonging to the field of medicinal chemistry. The general formula of the phenylpyrazolopyrimidine compound is that the compound has better PDE2 inhibitory activity, exhibits more excellent pharmacodynamic properties and has less side effects. This type of compound can be used to prepare medicines for treating senile dementia, depression, anxiety, cardiovascular and cerebrovascular diseases and the like.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a PDE2 inhibitor phenylpyrazolopyrimidine compound and a preparation method thereof. Background technique [0002] Cyclic adenosine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP) are important second messengers in the human body. They are distributed in various organs and affect various physiological activities of the human body. Changes in the concentration of cells in the body will cause various The occurrence of disease, therefore, how to maintain its normal concentration level has become the focus of research. Phosphodiesterases (PDEs) are the only family of super enzymes that can hydrolyze cAMP and cGMP in the body. There are 11 families of PDEs, whose expression is tissue- and cell-specific, and participates in the transduction process of various cellular pathways. Its inhibitors can regulate the concentration of intracellular cAMP and cGMP by...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61P25/28
CPCA61P25/28C07D487/04
Inventor 宋国强夏颜谈颖冯筱晴唐龙黄险峰曹依菁
Owner CHANGZHOU UNIV
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