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4-carbamate-3-methoxy cinnamic acid cyclamine alkyl amide compound, and preparation method and application thereof

A cinnamic acid cycloamine alkyl amide, carbamate technology, applied in organic chemistry, drug combination, muscle system diseases, etc., can solve the problems of single target, poor long-term efficacy in AD patients, and many toxic and side effects , to achieve the effects of high yield, good blood-brain barrier permeability, and simple and easy preparation method

Inactive Publication Date: 2016-08-10
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In view of this, the purpose of the present invention is to provide a kind of 4-carbamate-3-methoxycinnamic acid cyclic aminoalkylamide compound for the deficiencies in the prior art, which solves the problem of single drug target, More toxic and side effects, poor long-term curative effect on AD patients, etc.

Method used

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  • 4-carbamate-3-methoxy cinnamic acid cyclamine alkyl amide compound, and preparation method and application thereof
  • 4-carbamate-3-methoxy cinnamic acid cyclamine alkyl amide compound, and preparation method and application thereof
  • 4-carbamate-3-methoxy cinnamic acid cyclamine alkyl amide compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-19

[0038] A preparation method of 4-carbamate-3-methoxycinnamic acid cyclic amine alkyl amides compound, comprises the steps:

[0039] The first step: using phthalimide potassium salt as the starting material, reacting with 1-substituted-4-chloroalkylpiperidine in the first solvent and the first basic condition to obtain phthalimide imidoalkylamine compounds;

[0040] The second step: adding the phthalimide alkylamine compound obtained in the first step into the second solvent, adding N 2 h 4 .H 2 0, warming up to reflux and stirring reaction (reaction progress tracked with TLC); after the reaction was finished, suction filtration while hot, a small amount of ethanol washed the filter cake, the filtrate was evaporated under reduced pressure to remove the solvent, and the residue was purified by column chromatography (eluent: two Chloromethane:methanol=15:1v / v) to obtain alkylamino primary amine compounds;

[0041] The third step: the primary amine compound obtained in the sec...

Embodiment 20

[0067] The specific process conditions are the same as those in Example 1-2, and the difference is the same as in the investigation of different substituents. The specific substituents are shown in Table 5, and the resulting 4-carbamate-3-methoxycinnamic acid cyclic amine alkyl amides compound , and its chemical structure was confirmed by 1H-NMR, 13C-NMR and ESI-MS.

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

Embodiment 21

[0076] A kind of preparation method of the salt of 4-carbamate-3-methoxycinnamic acid cycloaminoalkyl amides compound, comprises the steps as follows, 4-carbamate-3-methoxycinnamic acid cycloaminoalkyl Mix the base amide compound (I) with acetone, stir evenly, add acid, heat and reflux and stir for 15 to 30 minutes, cool to room temperature after the reaction, evaporate the solvent under reduced pressure, recrystallize the residue with acetone, and filter the precipitated solid , to obtain the salt of 4-carbamate-3-methoxycinnamic acid cycloaminoalkylamide compound (I). Among them, its chemical structure was confirmed by 1HNR and ESI-MS.

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Abstract

The invention discloses a 4-carbamate-3-methoxy cinnamic acid cyclamine alkyl amide compound, and a preparation method and application thereof. The compound prepared in the invention has low toxic and side effect, and can treat neurodegenerative diseases including, but not limited to, vascular dementia, the Alzheimer's disease, the Parkinson's disease, the Huntington's disease, HIV-associated dementia, multiple sclerosis, amyotrophic lateral sclerosis, neuropathic pain, glaucoma and the like.

Description

technical field [0001] The present invention relates to an amide compound, a preparation method and its use, in particular to a 4-carbamate-3-methoxycinnamic acid cycloaminoalkylamide compound, a preparation method and its use, including but not Limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-related dementia, multiple sclerosis, progressive lateral sclerosis, neuropathic pain, glaucoma and other neurodegenerative diseases. Background technique [0002] Vascular dementia (AD) is a mental and cognitive disorder caused by various types of cerebrovascular diseases (including ischemic cerebrovascular disease, hemorrhagic cerebrovascular disease, acute and chronic hypoxic cerebrovascular disease, etc.). It is a clinical syndrome of cognitive dysfunction, and its main clinical manifestations include: decline in cognitive ability, memory, and social life ability, as well as changes in emotion and personality. It is a chronic progres...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/26A61P25/00A61P25/28A61P25/16A61P25/14A61P25/04A61P27/06A61P21/00
CPCC07D211/26
Inventor 桑志培柳文敏于林涛马勤阁陈长中潘万里李涛高利敏
Owner NANYANG NORMAL UNIV
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