N-(3- pyridine formex oxygen radical)-3, 5- dimethyl-1- amantadine or pharmaceutically-acceptable salt for treating vascular dementia

A picolinyloxy, vascular dementia technology, applied to N-(3-picolinyloxy)-3,5-dimethyl-1-adamantanamine or a pharmaceutically acceptable salt thereof for the treatment of vascular dementia In the field of dementia, it can solve the problems of slow drug absorption and excretion, accumulation of poisoning and side effects, lack of ability to analyze and judge diseases, and achieve the effect of increasing distribution concentration and action time, social value and clinical value, and reducing peripheral adverse reactions.

Inactive Publication Date: 2012-03-21
XIAN LIJUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

4. The situation at the time of onset is different: vascular dementia often has an acute onset, and the family members of the patients can generally tell the time of onset accurately; while the onset of senile dementia is mostly insidious, with no obvious time limit, and the patient's affiliation often cannot be identified. State the exact time of its onset
6. Patients have different attitudes towards the disease: patients with vascular dementia have a certain ability to understand their own symptoms such as memory loss, intellectual decline, emotional changes, and physic

Method used

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  • N-(3- pyridine formex oxygen radical)-3, 5- dimethyl-1- amantadine or pharmaceutically-acceptable salt for treating vascular dementia
  • N-(3- pyridine formex oxygen radical)-3, 5- dimethyl-1- amantadine or pharmaceutically-acceptable salt for treating vascular dementia
  • N-(3- pyridine formex oxygen radical)-3, 5- dimethyl-1- amantadine or pharmaceutically-acceptable salt for treating vascular dementia

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0213] Example 1

[0214] Preparation of N-(3-pyridinecarboxyloxy)-3,5-dimethyl-1-adamantamine by DCC / DMAP method (active ester method)

[0215] 2.46g (0.02mol) niacin and 4.32g (0.02mol) memantine hydrochloride were dissolved in dry 120mL DMF at room temperature, 2.30mL anhydrous TEA was added dropwise and 0.30g (0.002mol) DMAP was added, and stirred uniformly. Add 6.19g (0.03mol) DCC in 50mL DMF solution dropwise at 0-5℃, stir overnight at room temperature, filter, concentrate under reduced pressure, add appropriate amount of ethyl acetate, filter, and then water, 0.1N HCl, saturated NaHCO 3 , Washed with saturated brine 3 times, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and flash column chromatography (silica gel H, washing liquid: petroleum ether-acetone) to obtain N-(3-pyridinecarbonyloxy)-3,5 -Dimethyl-1-amantadine, a colorless viscous substance, 3.58 g, yield 63%.

[0216] MS (EI), m / z: 284 (M + ), 269 (M + -CH 3 ), 178(C 12 H 20 NO + ), 106...

Example Embodiment

[0221] Example 2

[0222] CDI / DMAP method (active ester method) to prepare N-(3-pyridinecarboxyloxy)-3,5-dimethyl-1-adamantamine

[0223] 0.62g (5mmol) niacin was dissolved in dry 25mL DMF solution, 0.81g (0.002mol) CDI and 0.08g (0.5mmol) DMAP were quickly added, and the reaction was stirred at 0-5°C for 1h. Add 1.08g (5mmol) memantine hydrochloride in 2.30mL anhydrous TEA and 25mL DMF solution mixed solution, stir overnight at room temperature, concentrate under reduced pressure, add appropriate amount of ethyl acetate, filter, and then water, 0.1N HCl, saturated NaHCO 3 , Washed with saturated brine 3 times, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and flash column chromatography (silica gel H, washing liquid: petroleum ether-acetone) to obtain N-(3-pyridinecarbonyloxy)-3,5 -Dimethyl-1-amantadine, a colorless viscous substance, 0.99 g, yield 70%.

Example Embodiment

[0224] Example 3

[0225] Preparation of N-(3-pyridinecarbonyloxy)-3,5-dimethyl-1-adamantamine by mixed acid anhydride method

[0226] Dissolve 0.32g (2.60mmol) of niacin in an appropriate amount of anhydrous CH under ice and salt bath 2 Cl 2 1mL (7.18mmol) TEA and 0.4mL (3.13mmol) of anhydrous benzenesulfonyl chloride were slowly added dropwise successively, stirred for 1h, and 0.40g (1.86mmol) of memantine hydrochloride and TEA CH were added. 2 Cl 2 The mixed solution was stirred and reacted for 3h, concentrated under reduced pressure, added appropriate amount of ethyl acetate, filtered, and then water, 0.1N HCl, saturated NaHCO 3 , Washed with saturated brine 3 times, dried over anhydrous magnesium sulfate, concentrated under reduced pressure to obtain a red oil, which was separated and purified by column chromatography (silica gel H, eluent: petroleum ether-acetone mixed solvent) to obtain N-(3-pyridine methyl) (Acyloxy)-3,5-dimethyl-1-adamantanamine, a colorless viscous substan...

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Abstract

The invention relates to application of N-(3- pyridine formex oxygen radical)-3, 5- dimethyl-1- amantadine or pharmaceutically-acceptable salt for treating vascular dementia.

Description

Technical field: [0001] The present invention relates to a new indication of N-(3-pyridineformyloxy)-3,5-dimethyl-1-adamantanamine or a pharmaceutically acceptable salt thereof, that is, its role in the treatment of vascular dementia application. Background technique: [0002] Vascular dementia is dementia caused by cerebrovascular disease, such as multiple infarctions and cerebral hemorrhage, which is mainly caused by the narrowing and blockage of cerebral blood vessels after cerebral arteriosclerosis, and insufficient oxygen and blood supply to the brain. Previously called multi-infarct dementia (multi-infarct dementia, referred to as MID), the newly published diagnostic classification system has been renamed as vascular dementia (vascular dementia, referred to as VD). VD is more common in the elderly over 60 years old with arteriosclerosis, more men than women. The incidence of vascular dementia is very high, and about 1 / 4 of stroke survivors may occur. Statistics show...

Claims

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Application Information

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IPC IPC(8): A61K31/465A61P25/28A61P9/10
CPCA61K9/0095A61K9/2018A61K9/4866A61K31/455A61P9/10A61P25/28
Inventor 熊晓云苏建英唐柳张敬乐赵艳菊杜春梅
Owner XIAN LIJUN PHARMA CO LTD
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