Compound with clam and hypnosis functions, and preparation method and application thereof

A compound and drug technology, applied in the field of sedative and hypnotic compounds, can solve problems such as restricting the clinical application of drugs

Inactive Publication Date: 2015-02-25
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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  • Compound with clam and hypnosis functions, and preparation method and application thereof
  • Compound with clam and hypnosis functions, and preparation method and application thereof
  • Compound with clam and hypnosis functions, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Example 1 Preparation of N-ethyl-N-3-[7-aminomethylpyrazolo[1,5a]pyrimidinylphenyl]acetamide

[0088]

[0089] The processing steps of the present embodiment are as follows:

[0090] 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 mixture of acetamide in DMF solution was cooled with ice water at 0°C, 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.145-147°C;

[0091]...

Embodiment 2

[0093] Example 2 Preparation of N-ethyl-N-3-[7-(3-N-n-propylaminomethylpyrazolo[1,5a]pyrimidinyl)phenyl]acetamide (4a for short)

[0094]

[0095] The processing steps of the present embodiment are as follows:

[0096] 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, after dissolving, continue to add 0.12mmol n-bromopropane, react at room temperature for 2h after the addition, after TLC tracking the reaction, 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-ethyl-N-3-[7-(3-N-n-propylaminomethylpyrazolo[1,5a]pyrimidinyl)phenyl] Acetamide, white powdery solid, yield 96%, m.p.111-116°C; 1 H NMR (400MHz, CDCl 3 )δ(ppm):1.00(t,J=7.2Hz,3H),1.08(t,J=7.0Hz,3H),1.73(m,2H),1.79(s,3H),2....

Embodiment 3

[0097] Example 3: Preparation of N-ethyl-N-3-[7-(3-N-isopropylaminomethylpyrazolo[1,5a]pyrimidinyl)phenyl]acetamide (abbreviated as 4b)

[0098]

[0099] 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 isobromopropane after dissolving, react at room temperature for 2h after the addition, after TLC tracking the reaction, 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-ethyl-N-3-[7-(3-N-isopropylaminomethylpyrazolo[1,5a]pyrimidinyl)phenyl] Acetamide, white powdery solid, yield 92%, m.p.179-180°C; 1 H NMR (400MHz, CDCl3 )δ(ppm): 1.08(t, J=7.2Hz, 3H), 1.26(d, J=6.8Hz, 3H), 1.30(d, J=6.4Hz, 3H), 1.79(s, 3H), 2.23 (m,1H),2.49(m,1H),3.00(td,J=11.6Hz,2.8Hz,1H...

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Abstract

The invention discloses a compound expressed in a formula 1. The structural formula of the compound is as follows, wherein R is alkyl group with H and C1-10, -COOR1, -CH2-C6H4-R2, the R1 is alkyl group with the H or the C1-10, the R2 is H, halogen, nitro or alkyl group with C1-5, and R3 is alkyl group with C1-5, arene group of C6-12 or substitutional alkyl group of C1-5. The invention also provides the application of the compound. The compound disclosed by the invention can obviously inhibit spontaneous movement times of a mouse, and the compound has a significance difference or an extreme significance difference by comparing each time point and a negative contrast group, so that the compound can be used as a medical active ingredient of a medicine preventing insomnia and further can be used for developing new medicines which are relatively good in medical effect and relatively small in untoward effect, thus having obvious social benefits and economic benefits. The method provided by the invention has the advantages that the method process line is very simple, the cost is relatively low, the yield of products is relatively high, and the requirements on industrial and large-scale production can be met.

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 is an important nitrogen-containing heterocyclic structure in medicinal chemistry and has been widely concerned by the industry 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)...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/519A61P25/20
Inventor 尹述凡王裕军李霞袁明兴董林李颖
Owner SICHUAN UNIV
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