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Carbamate compounds, preparation method and application thereof

A technology of carbamates and compounds, applied in the field of carbamates, their preparation and application, can solve the problems of multiple toxic and side effects, single action target, poor long-term curative effect of AD patients, etc.

Inactive Publication Date: 2012-12-12
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs have problems such as single target, many toxic and side effects, and poor long-term curative effect on AD patients.

Method used

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  • Carbamate compounds, preparation method and application thereof
  • Carbamate compounds, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] ( E )- N,N - Preparation of 4-(3,5-dimethoxystyryl)phenyl dimethylcarbamate (I-3-1)

[0030] Add pterostilbene (2.0 mmol), K 2 CO 3 (3.0 mmol) and acetonitrile (20 ml), stir well and add N,N -Dimethylcarbamoyl chloride (3.0 mmol), reacted with stirring at room temperature for 15 hours (the reaction progress was followed by TLC); Dehydration: petroleum ether / ethyl acetate=5:1v / v) to obtain a white powder solid with a yield of 84.2%, mp: 124~125°C, HR-TOFMS (+Q) m / z :328.1557 ([C 19 h 21 NO 4 +H] + Calculated: 328.1549).

Embodiment 2

[0032] ( E )- N -methyl- N - Preparation of 4-(3,5-dimethoxystyryl)phenyl ethyl carbamate (I-3-2)

[0033] Operation process is the same as embodiment 1, just acetonitrile is replaced with chloroform, K 2 CO 3 Replaced with triethylamine, N,N -Dimethylcarbamoyl chloride N -methyl- N -Ethylcarbamoyl chloride was substituted to give a white powder solid with a yield of 79.3%, mp: 66.6~67.6℃, HR-TOFMS (+Q) m / z :342.1701 ([C 20 h 23 NO 4 +H] + Calculated: 342.1705).

Embodiment 3

[0035] ( E )- N,N - Preparation of 4-(3,5-dimethoxystyryl)phenyl diethylcarbamate (I-3-3)

[0036] Operation process is the same as embodiment 1, just will N,N -Dimethylcarbamoyl chloride N,N -Diethylcarbamoyl chloride was substituted to obtain a white powder solid with a yield of 82.7%, mp: 53.5~54.5°C, HR-TOFMS (+Q) m / z :356.1855 ([C 21 h 25 NO 4 +H] + Calculated value: 356.1862).

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Abstract

The invention discloses novel carbamate compounds (I-1 to I-4) and pharmaceutically acceptable salts thereof, a preparation method of the compounds, and application of the compounds in preparation of medicines for preventing neurodegenerative diseases, including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV (human immunodeficiency virus) related cretinism, multiple sclerosis, progressive lateral spinal sclerosis, neuropathic pain, glaucoma and the like.

Description

technical field [0001] The present invention belongs to the field of medicinal chemistry and relates to a new type of carbamate compound (I), in particular to carbamate derivatives of resveratrol, dihydroresveratrol, pterostilbene or dihydropterostilbene and Its pharmaceutically acceptable salt, its preparation method, pharmaceutical composition and use in the preparation of medicines for the treatment and / or prevention of neurodegenerative related diseases, including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease neurodegenerative diseases, Huntington's disease, HIV-related dementia, multiple sclerosis, progressive lateral sclerosis, neuropathic pain, glaucoma, etc. Background technique [0002] Vascular dementia (VD) 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.). ...

Claims

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Application Information

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IPC IPC(8): C07C271/44C07C271/54C07C269/00C07C269/02C07D295/205C07D211/16C07D243/08A61K31/27A61K31/4453A61K31/4545A61K31/5375A61K31/5377A61K31/495A61K31/496A61K31/4025A61K31/40A61K31/445A61P25/28A61P25/16A61P25/04A61P27/06
Inventor 邓勇强晓明桑志培袁文白平
Owner SICHUAN UNIV
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