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Sedative and soporific compound, and preparation method and application thereof

A compound, phenyl technology, applied in the field of sedative and hypnotic compounds, can solve the problems restricting the clinical application of drugs, achieve the effect of inhibiting the number of spontaneous activities, simple process route, obvious social and economic benefits

Inactive Publication Date: 2012-11-14
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But at the same time, there are also many obvious side effects, such as back and chest pain, migraine, constipation, dry mouth, arthritis, depression, tension and hallucinations, etc., which also affect and restrict the clinical application of the drug

Method used

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  • Sedative and soporific compound, and preparation method and application thereof
  • Sedative and soporific compound, and preparation method and application thereof
  • Sedative and soporific compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Preparation of N-ethyl-N-3-[7-aminomethylpyrazolo[1,5a]pyrimidinylphenyl]acetamide (2 for short)

[0051]

[0052] The processing steps of the present embodiment are as follows:

[0053] In a 100mL pear-shaped flask, add 20mmol of ferric chloride hexahydrate in 10mL of aqueous solution and 10mmol of N-ethyl-N-3-[7-(3-cyanopyrazolo[1,5a]pyrimidinyl)phenyl ] The mixed liquid of DMF solution of acetamide was cooled with ice water at 00C, and 0.1mol sodium borohydride was added several times under stirring. After the addition was completed, it was reacted at room temperature for 5 hours, and the reaction was tracked by TLC. After the end, filter, extract with EA several times, wash with water several times, and the organic layer is washed with anhydrous Na 2 SO 4 Dry and spin dry, and the crude product is purified by column chromatography to obtain N-ethyl-N-3-[7-aminomethylpyrazolo[1,5a]pyrimidinylphenyl]acetamide as a white powdery solid , yield 58%, m.p.1...

Embodiment 2

[0056] Example 2: N-[7-(N-acetyl-N-ethylamino-3-)phenyl[pyrazolo[1,5a]pyrimidinyl]-3-]methylbenzenesulfonamide (abbreviated as 4a ) preparation

[0057]

[0058] The process steps of this embodiment are as follows: in a 25mL pear-shaped bottle, add 10mL THF, add 0.3mmol NaH under ice bath conditions, stir for 5 minutes, add 0.1mmol N-ethyl-N-3-[7-aminomethyl Pyrazolo[1,5a]pyrimidinylphenyl]acetamide, continue to add 0.12mmol benzenesulfonyl chloride after dissolving, react at room temperature for 1h after the addition, follow the reaction by TLC, extract with EA, wash with water, and use Anhydrous Na 2 SO 4 Drying and spin-drying, the crude product was purified by column chromatography to obtain N-[7-(N-acetyl-N-ethylamino-3-)phenyl[pyrazolo[1,5a]pyrimidinyl]-3 -] Toluenesulfonamide, white powdery solid, 92% yield, m.p.160-161°C. 1 H NMR (400MHz, CDCl 3 )δ(ppm):0.98(t,J=7.2Hz,3H),1.66(s,3H),1.89(m,1H),2.25(m,1H),3.59(q,J=7.2Hz,2H) ,3.74(m,1H),3.88(m,1H),5.26(t,J=6.8Hz...

Embodiment 3

[0059] Embodiment 3: N-[7-(N-acetyl-N-ethylamino-3-)phenyl[pyrazolo[1,5a]pyrimidinyl]-3-]methyl-p-bromobenzenesulfonamide ( Abbreviated 4b) Preparation

[0060]

[0061] The processing steps of the present embodiment are as follows:

[0062] The process steps of this embodiment are as follows: in a 25mL pear-shaped bottle, add 10mL THF, add 0.3mmol NaH under ice bath conditions, stir for 5 minutes, add 0.1mmol N-ethyl-N-3-[7-aminomethyl Pyrazolo[1,5a]pyrimidinylphenyl]acetamide, continue to add 0.12mmol benzenesulfonyl chloride after dissolving, react at room temperature for 1h after the addition, follow the reaction by TLC, extract with EA, wash with water, and use Anhydrous Na 2 SO 4 Drying and spin-drying, the crude product was purified by column chromatography to obtain N-[7-(N-acetyl-N-ethylamino-3-)phenyl[pyrazolo[1,5a]pyrimidinyl]-3 -] Methyl-p-bromobenzenesulfonamide, white powdery solid yield 89%, m.p.137-139°C. 1 H NMR (400MHz, CDCl 3 )δ(ppm):1.08(t,J=7.2Hz,...

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Abstract

The invention discloses a compound shown in a formula I. In the formula I, R is H, -SO2 or -Ar; and Ar is a C6-12 aromatic alkyl or substituted aromatic alkyl. The invention also provides a preparation method and application of the compound. The compound provided by the invention can obviously inhibit the spontaneous activity frequency of mice, and the comparison with a negative control group at each time point shows significant and highly-significant differences, so that the compound can be used as a medical active component of an anti-insomnia medicament to facilitate the development of a new medicament having a better effect, thereby achieving obvious social benefits and economic benefits. The method disclosed by the invention is very simple in process route, low in cost and high in product yield, and is suitable for requirements of industrialized and expanded production.

Description

technical field [0001] The invention relates to a sedative and hypnotic compound, its preparation method and application. Background technique [0002] Pyrazolo[1,5-a]pyrimidine, an important nitrogen-containing heterocycle in organic chemistry and medicinal chemistry, has been widely concerned for a long time. Since the molecule has two important active units of pyrazole and pyrimidine, these compounds often have good biological activity. A large number of compounds containing pyrazolopyrimidine structural units have been used in the field of medicine, and their derivatives can be Acting on multiple important biological targets, showing a wide range of pharmacological activities, such as cell cycle-dependent protein kinases (CDKs) inhibitors, cell cycle checkpoint kinase inhibitors, hydroxymethylglutaryl-CoA (HMG- CoA) reductase inhibitors, cyclooxygenase (COX-2) selective inhibitors, adenosine monophosphate (AMP) phosphodiesterase inhibitors, serotonin 6 (5-HT6) receptor ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/519A61P25/20
Inventor 尹述凡王裕军宋长伟蒋丽娟董林李颖
Owner SICHUAN UNIV
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