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Phylloline derivatives and their pharmaceutical compositions and their application in pharmacy

A technology of anophylline and its derivatives, which is applied in the field of anophylline derivatives 1-2 and their pharmaceutical compositions, and can solve problems such as those that have not been reported

Active Publication Date: 2019-01-22
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is no report on the medicines of the anophylline derivatives (1-2) provided by the present invention as melatonin and 5-hydroxytryptamine receptor agonists and active ingredients for antipsychotic diseases, and its derivatives or pharmaceutical compositions thereof are used as Melatonin and serotonin receptor agonists have not been reported in the preparation or treatment of antipsychotic drugs

Method used

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  • Phylloline derivatives and their pharmaceutical compositions and their application in pharmacy
  • Phylloline derivatives and their pharmaceutical compositions and their application in pharmacy
  • Phylloline derivatives and their pharmaceutical compositions and their application in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0025] Phylloline (2mmol) and N-tert-butoxycarbonyl-homopiperazine (2mmol) were dissolved in 10 mL of anhydrous toluene, refluxed at 110°C until the end of the reaction, and the solvent was recovered under reduced pressure to prepare a crude product, which was prepared by silica gel column layer Purify by analysis (diethylamine / methanol / chloroform=2 / 4 / 94) to obtain the target compound (1).

[0026] Compound 1 structure determination data:

[0027] N-tert-Butyloxycarbonyl-N-homopiperazinyl-3-indolylmethylamine (N-tert-Butyloxycarbonyl-N-homopiperazinyl-3-indolymethylamine,

[0028]

[0029] 1.85-1.82(m,2H,H-3'),1.49(s,9H,Me-Boc). 13 C NMR (100MHz, CDCl 3 )δ:155.7(s,C-8),136.4(s,C-8),127.9(s,C-9),123.8(d,C-2), 121.8(d,C-6),119.5( d,C-5),119.3(d,C-4),112.8(s,C-3),111.2(d,C-7),79.4(s,C-Boc),55.77(t,C-7 '),54.7(t,C-2'),53.5(t,CHN),46.8(t,C-6'),46.2(t,C-4'),28.6(s,C-Me-Boc) ,27.9(t,C-3').ESIMS:m / z 330 [M+H] + ,HRESIMS:C 19 h 27 N 3 o 2 [M+H] + The measured value is 330...

preparation Embodiment 2

[0031] Phylloline (4mmol), dissolved in 10mL of anhydrous toluene with 2-aminoethylpiperazine (2mmol), refluxed at 110°C until the end of the reaction, recovered the solvent under reduced pressure, prepared a crude product, and performed silica gel column chromatography ( Diethylamine / methanol / chloroform=3 / 5 / 92) to obtain the target compound (2).

[0032] Compound 2 structure determination data:

[0033] N-(N-3-indolylmethylaminoethyl)-N-piperazinyl-3-indolylmethylamine [N-[N-(3-indolymethyl)-aminoethyl]-N-Piperazinyl-3-indolylmethyla

[0034]

[0035] mine,2]: white powder, yield 70%. 1 H NMR (CDCl 3 ,400MH Z )δ H:8.72(s, 2H,NH),7.72-7.01(m,10H,H-2,2',4,4',5,5',6,6',7,7'),3.98(s, 2H, CH 2 N),3.72(s,2H,CH 2 CH 2 NH CH 2 ),3.45(s,1H,CH 2 CH 2 NH CH 2 ), 2.79-2.77(m,2H,CH 2 CH 2 NHCH 2 ),2.69-2.68(m,2H, CH 2 CH 2 NHCH 2 ), 2.52-2.42(m,4H,H-3',5'),2.20-2.18(m,4H,H-2',6'). 13 C NMR (100 MHz, CDCl 3 )δ:136.4(s,C-8,8'),128.1(s,C-9),127.0(s,C-9'),124.1(...

preparation Embodiment 1

[0051] The anophylline derivatives 1-2 prepared according to the method of Preparation Example 1 were dissolved in a small amount of DMSO separately or in combination, and then water for injection was added as usual, finely filtered, potted and sterilized to make an injection.

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Abstract

The invention belongs to the technical field of medicines, and in particular relates to anophylline derivatives (1-2), pharmaceutical compositions and preparation methods thereof, and such derivatives or pharmaceutical compositions as melatonin and 5-serotonin receptor agonists and its application in the preparation of antipsychotic drugs, especially in the preparation of drugs for treating or improving central nervous system diseases related to melatonin and 5-hydroxytryptamine receptors.

Description

technical field [0001] The present invention belongs to the technical field of medicines, in particular, it relates to anophylline derivatives 1-2 and their pharmaceutical compositions, their preparation methods and their use in the preparation and treatment of central nervous system diseases related to melatonin and 5-hydroxytryptamine receptors. application in medicine. Background technique [0002] Melatonin receptor is a neuroendocrine hormone secreted by the pineal gland. It is controlled by the suprachiasmatic nucleus of the hypothalamus and can regulate the circadian rhythm. This rhythmic fluctuation shows that it reaches a peak at night and drops to a valley during the day. McCord and Allan discovered in 1917 that the bovine pineal gland can regulate changes in the skin of Rana pipien tadpoles in the environment, and determined the structure of melatonin as N-acetyl-5-methoxytryptamine. According to the function and pharmacological properties of melatonin, melatonin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/06C07D209/14A61K31/551A61K31/496A61P25/00A61P25/28
CPCC07D209/14C07D403/06
Inventor 陈纪军尹秀娟耿长安马云保黄晓燕张雪梅
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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