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Pyrimidine derivatives and application thereof

A technology of pyrimidines and derivatives, which is applied to pyrimidine derivatives and its application in the treatment of pain diseases, can solve the problems of low response rate, large side effects of drugs, easy generation of drug resistance and addiction, etc.

Active Publication Date: 2014-12-17
武汉久安药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the clinical treatment of neuralgia, there are no specific methods and effective drugs. In general, neuropsychiatric drugs are used as adjuvant therapy. The main drugs used are: 1) Neurotransmitter reuptake inhibitors such as antidepressants (such as amitriptyline; and the newly listed duloxetine), these drugs have relatively large side effects and low response rate; 2) Calcium ion channel α 2 -δ ligand antiepileptic drugs (such as gabapentin and pregabalin), the effective rate of such drugs is limited, about 40%, and individual differences are obvious; 3) Opioid receptor analgesics; such drugs are prone to drug resistance and addiction, and the adverse reactions are obvious

Method used

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  • Pyrimidine derivatives and application thereof
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  • Pyrimidine derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1, 4-methyl-2-phenyl-6-(2-(morpholin-1-yl)ethoxy)pyrimidine (1)

[0091] Reaction 1

[0092]

[0093]1) Dissolve 12.0 g of benzamidine and 13.0 g of ethyl acetoacetate in 200 ml of methanol, stir in an ice bath, and cool to 0°C. Take 2.3 g of potassium tert-butoxide, add slowly, remove the ice bath after the addition, and stir to room temperature. Then heated to reflux and reacted for 6 hours. After the reaction was completed, 500 ml of distilled water was added, and the pH was adjusted to be neutral with 10% citric acid solution, and a white solid was precipitated. After filtering, the solid was washed twice with water, and recrystallized from 95% ethanol to obtain 11.3 g of white solid with a melting point of 218-221° C. and a yield of 60.7%.

[0094] 2) Take 9.3g of the first step product, 13.8g of anhydrous potassium carbonate, 18.8g of 1,2-dibromoethane, add 100ml of acetone, heat and reflux for 4 hours, cool to room temperature, filter, and evaporate...

Embodiment 2

[0097] Example 2, 4-methyl-2-phenyl-6-(3-(morpholin-1-yl)propoxy)pyrimidine (2)

[0098] Replace 1,2-dibromoethane with 1,3-dibromopropane, and prepare the target compound according to the method of Example 1.

[0099] 1 H NMR (600 MHz, CDCl 3 )δ8.45–8.41(m,2H),7.45–7.40(m,3H),6.44(s,1H),4.52(t,J=6.5Hz,2H),3.71(t,J=4.6Hz,4H ), 2.57–2.39(m,9H), 2.05–1.94(m,2H). MS(ESI) m / z 313.2([M+H] + )

Embodiment 3

[0100] Example 3, 4-methyl-2-phenyl-6-(4-(morpholin-1-yl)butoxy)pyrimidine (3)

[0101] Replace 1,2-dibromoethane with 1,4-dibromobutane, and prepare the target compound according to the method of Example 1.

[0102] 1 H NMR (600 MHz, CDCl 3 )δ8.45–8.41(m,2H),7.46–7.41(m,3H),6.44(s,1H),4.49(t,J=6.5Hz,2H),3.70(t,J=4.6Hz,4H ),2.48(s,3H),2.45–2.38(m,6H),1.88–1.80 (m,2H),1.71–1.63(m,2H).MS(ESI)m / z 328.2([M+H] + )

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PUM

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Abstract

The invention discloses compounds of formula (1), and pharmaceutically acceptable salts thereof, and an application of the compounds and the pharmaceutically acceptable salts in prevention and treatment of aches.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a pyrimidine derivative and its application in treating pain diseases. Background technique [0002] Pain is a basic feeling that human beings possess naturally, and it plays an important role in protecting the human body from injury and maintaining the internal environment of the human body. However, long-term or excessive pain can seriously affect people's normal physiological life. Chronic pain and neuralgia are medically defined as diseases that seriously endanger human health. Neuralgia is one of the most harmful diseases among pain diseases, affecting about 8% of the world's population. The onset of neuralgia is sudden, severe, and difficult to cure. Although researchers have done a lot of related work in the fields of basic research and clinical research, there are still huge challenges in clinical research on neuralgia and the analgesic mechanism. Due to t...

Claims

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Application Information

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IPC IPC(8): C07D239/34C07D401/12C07D403/12A61K31/551A61K31/506A61K31/505A61P25/04A61P25/00
CPCC07D239/34C07D401/12C07D403/12
Inventor 张桂森兰昱林亚维
Owner 武汉久安药业有限公司
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