Gramine derivative, drug combination thereof and application thereof to 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: 2017-06-30
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 ...

Method used

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  • Gramine derivative, drug combination thereof and application thereof to pharmacy
  • Gramine derivative, drug combination thereof and application thereof to pharmacy
  • Gramine derivative, drug combination thereof and application thereof to pharmacy

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0024] Phylloline (2mmol) and N-tert-butoxycarbonyl-homopiperazine (2mmol) were dissolved in 10mL 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 subjected to silica gel column chromatography Purification (diethylamine / methanol / chloroform=2 / 4 / 94) gave the target compound (1).

[0025] Compound 1 structure determination data:

[0026] N-tert-butoxycarbonyl-N-homopiperazinyl-3-indolylmethylamine (N-tert-Butyloxycarbonyl-N-homopiperazinyl-3-indolymethylamine, 1): yellow powder, yield 82%. 1 H NMR (400MHz, CDCl 3 )δ H : 8.91(s, 1H, NH), 7.76-7.03(m, 5H, H-2, 4, 5, 6, 7), 3.83(s, 2H, CH 2 N), 3.55-3.43(m, 4H, H-2', 4'), 2.72-2.66(m, 4H, H-6', 7'), 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 ...

preparation Embodiment 2

[0028] 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).

[0029] Compound 2 structure determination data:

[0030] N-(N-3-indolylmethylaminoethyl)-N-piperazinyl-3-indolylmethylamine[N-[N-(3-indolymethyl)-aminoethyl]-N-Piperazinyl-3-indolylmethylamine , 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 (100MHz, CDCl 3 )δ: 136.4 (s, C-8, 8′), 128.1 (s, C-...

preparation Embodiment 1

[0045] 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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PUM

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Abstract

The invention belongs to the technical field of drug, and particularly relates to gramine derivative (1-2), a drug combination thereof, a preparation method thereof, application of the derivative or the drug combination serving as a melatonin and 5-serotonin receptor agonist, application of the derivative or the drug combination to the preparation of drugs resisting mental diseases, and particularly application of the derivative or the drug combination to the preparation of drugs for treating and improving central nervous system diseases related to melatonin and 5-serotonin receptor.

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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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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