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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 physical discomfort, and hope to be treated; The disease they suffer from lacks the ability to analyze and judge, and some patients even think that they are in good health and do not need treatment
5. Drugs to improve mental symptoms: anti-anxiety and anti-depressant drugs, such as Suloazepam, Jiajingan, Rolla, and Doxepin; can improve some symptoms
In addition, there are few types of drugs currently used to treat the disease, a single target, and poor long-term efficacy. Clinically, there is an urgent need to research and develop novel, effective and safe VD therapeutic drugs.

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

Embodiment 1

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

[0215] 2.46g (0.02mol) of nicotinic acid and 4.32g (0.02mol) of memantine hydrochloride were dissolved in dry 120mL DMF at room temperature, 0.30g (0.002mol) of DMAP was added dropwise after adding 2.30mL of anhydrous TEA, and stirred evenly. Add 6.19g (0.03mol) DCC solution in 50mL DMF dropwise at 0-5°C, stir overnight at room temperature, filter, concentrate under reduced pressure, add an appropriate amount of ethyl acetate, filter, then water, 0.1N HCl, saturated NaHCO 3 , saturated brine for 3 times, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, flash column chromatography (silica gel H, washing solution: petroleum ether-acetone), to obtain N-(3-pyridineformyloxy)-3,5 - Dimethyl-1-adamantanamine, 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(C ...

Embodiment 2

[0222] Preparation of N-(3-pyridyloxy)-3,5-dimethyl-1-adamantanamine by CDI / DMAP method (active ester method)

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

Embodiment 3

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

[0226] Dissolve 0.32g (2.60mmol) niacin in an appropriate amount of anhydrous CH under ice-salt bath 2 Cl 2 1mL (7.18mmol) TEA and 0.4mL (3.13mmol) anhydrous benzenesulfonyl chloride were slowly added dropwise in sequence, stirred for 1h, and 0.40g (1.86mmol) of memantine hydrochloride and TEA’s CH 2 Cl 2 The mixed solution was stirred for 3 h, concentrated under reduced pressure, added an appropriate amount of ethyl acetate, filtered, followed by water, 0.1N HCl, saturated NaHCO 3 , saturated brine for 3 times, dried over anhydrous magnesium sulfate, and 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-pyridinemethyl Acyloxy)-3,5-dimethyl-1-adamantanamine, colorless viscous substance, 0.41 g, yield 77%.

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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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