Unlock instant, AI-driven research and patent intelligence for your innovation.

Symmetrel derivatives and synthesis method thereof and their use as neuron damage protective agent

A technology of amantadine and its derivatives, which is applied to the preparation of amine active ingredients, carbamic acid derivatives, and medical preparations containing active ingredients, etc.

Inactive Publication Date: 2007-11-28
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compound involved in the present invention and the study of nerve injury protective effect thereof, have not seen relevant report so far

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Symmetrel derivatives and synthesis method thereof and their use as neuron damage protective agent
  • Symmetrel derivatives and synthesis method thereof and their use as neuron damage protective agent
  • Symmetrel derivatives and synthesis method thereof and their use as neuron damage protective agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1.1-methoxyacyl-3,5-dimethylamantadine (M 1-1 )Synthesis

[0044] Add triethylamine (0.24ml, 1.7mmol) to M 1 (300mg, 1.67mmol) in THF solution, after stirring for 10 minutes, ice-water bath and N 2 Under protection, methoxyl chloride (1.67 mmol) was added dropwise to the mixture, and stirred at room temperature for 3 hours. Filter the reaction solution, rinse the insoluble matter with THF, combine the filtrate, add 2 g of silica gel, stir for 40 minutes, evaporate the solvent and transfer to a silica gel column, wash with the eluent (haxane:EA=25:1), and concentrate the eluate 0.37 g of amide was obtained with a yield of 93%. The structural identification data are as follows:

[0045] m 1-1 : 1 HNMR (ppm, CDCl 3 ): 0.82 (s, 6H, 2CH 3 , 1.07(s, 2H, 4-CH 2 ), 1.2-1.5 (m, J=12, 4H, 7, 9-2CH 2 ), 1.5-1.6 (s, 4H, 2, 6-2CH 2 ), 1.75 (d, J=2.4, 2H, 10-CH 2 ), 2.08-2.10 (m, 1H, 8-CH), 3.6 (s, 3H, -OCH 3 ), 4.58(s, -NH).

[0046] FAB-MS: [2M + +1] 475.3...

Embodiment 2

[0047] Embodiment 2.N-methoxyacyl amantadine (Ad 1 )Synthesis

[0048] With the similar method with embodiment 1, synthetically obtains N-methoxyacyl adamantamine (Ad 1 ), the yield is 89%.

[0049] The structural identification data are as follows:

[0050] ad 1 : 1 HNMR (ppm, CDCl 3 ): 1.66 (m, 6H, 3CH 2 ), 1.9(m, 6H, 3CH 2 ), 2.09(m, 3H), 3.6(s, 3H, OCH 3 ).

[0051] FAB-MS: [M + +1] 210.1, mp: 90°C (crystal change), 112°C (melting).

Embodiment 3

[0052] Embodiment 3.N-isopropoxyacyl-3,5-dimethylamantadine (M 1-2 )Synthesis

[0053] With the similar method with embodiment 1, synthetically obtains M 1-2 , yield 79%. The structural identification data are as follows:

[0054] m 1-2 : 1 HNMR (ppm, CDCl 3 ): 0.82 (s, 6H, 2CH 3 ), 1.07 (d, J=1.8Hz, CH 2 ), 1.2(m, 6H, 2CH3), 1.1-1.4(m, 6H, 3CH 2 ), 1.6(m, 4H, 2CH2), 1.76(s, 2H, CH 2 ), 2.08-2.10 (m, 1H, CH), 4.42 (s, -NH), 4.83 (m, 1H, CH).

[0055] FAB-MS: [M + +1] 266.1.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to symmetrel derivatives and their synthesis process and use as neuron damage protector. Said symmetrel derivatives are N-alkyl monosubstituted, N-alkyl disubstituted and N-acidylated derivative of symmetrel compounds. In vitro experiment shows that the tested compounds can make the growth of damaged neuron SY5Y normal under condition of some concentration.

Description

Technical field: [0001] The present invention relates to the structure of N-hydrocarbyl monosubstituted, N-hydrocarbyl disubstituted and N-acylated derivatives of amantadine compounds, their synthetic methods and their application in the protection of nerve damage. Compounds have laid the foundation for the prevention and treatment of neurodegenerative diseases. Background technique: [0002] Studies have shown that 70% of brain cells use glutamate as a neurotransmitter for rapid signal transduction. The neurosynaptic receptor activated by glutamate is the N-methyl-D-aspartate (NMDA) glutamate receptor. Excessive excitation of NMDA receptors leads to intrasynaptic Ca 2+ If the concentration is too high, the signal conduction background noise will increase, so that the information changes during learning or memory are not obvious or difficult to recognize, manifested as dementia (McBrain CJ et al, Physiol. Rev 74:723-760, 1994). Chronic cranial neurological diseases such a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/38C07C209/68C07C271/24C07C269/04C07C233/57C07C231/10A61K31/13A61K31/325A61P25/00
Inventor 李卓荣李艳萍刘宗英
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI