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Pentoxifylline derivative

A technology of theobromine derivatives and hexanone, applied in the directions of drug combination, active ingredients of heterocyclic compounds, cardiovascular system diseases, etc., can solve problems such as pain of patients, and achieve the effect of good vasodilation and neuroprotection.

Inactive Publication Date: 2010-02-17
徐奎
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] If a stroke is survived, it usually leaves permanent damage such as numbness, crooked eyes, central paralysis, peripheral paralysis, hemiplegia, aphasia, agnosia, and apraxia, which necessitate long-term care and great suffering , the burden of relatives already spending on health services is equally heavy

Method used

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Examples

Experimental program
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Effect test

preparation example 1

[0036] Preparation Example 1: Preparation of Intermediate I: (N-Methyl-N-Hydroxyethyl) Aminomethyl Chlorohydrin

[0037] 1. Preparation of N-methylethanolamine

[0038] In a 2000ml four-neck flask, install an electric stirrer, a reflux condenser, a thermometer, and a gas absorption device, add 220.4g (7.097mol) of 25% to 40% methylamine aqueous solution, and stir at 25 to 40°C. Ethylene oxide gas is 58.2g (7.096mol). After ventilation is completed, heat and stir slowly to 120°C, carry out distillation, collect fractions at 120-180°C, and conduct secondary distillation to control the collection of n D 20 The fraction of 1.4385 is 45.6 g of N-methylethanolamine, which is directly reacted in the next step.

[0039] 2, the preparation of (N-methyl-N-hydroxyethyl) aminomethyl chloroethanol

[0040] Add 37g (0.4mol) of epichlorohydrin and 20ml of isopropanol (i-PrOH) into the reaction flask, stir to dissolve, cool down to 18-22°C, and add 37.5g of the compound prepared in the above...

preparation example 2

[0041] Preparation Example 2: Preparation of Compound 3-Methyl-7-[2'-Hydroxy-3'-[(2-Hydroxymethyl)methylamino]Propyl]Xanthine

[0042] In the reaction flask, add 125ml of absolute ethanol and 2.86g (0.124) of sodium metal, stir to completely dissolve the metal sodium, then add 20.8g (0.124mol) of powdered 3-methylpurine, heat and reflux for 10 minutes to obtain 3- Sodium salt of methylpurine. Slowly add 20.7 g (0.124 mol) of the isopropanol solution of 1 / 4 (N-methyl-N-hydroxyethyl) aminomethyl chloroethanol in the above preparation example 1 dropwise, stir and reflux after adding, and thin-layer identification At the end of the reaction (developer: ethyl acetate: ethanol: glacial acetic acid = 5:2; 0.1, v:v:v), the reaction was completed in about 4.5 hours. Cool to 0~-5°C, filter, then dissolve the solid with an appropriate amount of 1N NaOH solution, adjust the pH value with 0.5N HCl, control the pH value to 11.5, filter the obtained solid, and use 200ml methanol / chloroform=...

Embodiment 1

[0044] Example 1: Compound 1-(5'-oxohexyl)-3-methyl-7-[2'-hydroxyl-3'-[(2-hydroxymethyl)methylamino]propyl]xanthine. preparation of

[0045] In a 500ml four-necked flask, install an electric stirrer, a reflux condenser, a thermometer and N 2 To the airway, add 27g (0.09mol) of the compound of Preparation Example 2, 16.8g (0.158mol) of anhydrous potassium carbonate and 250ml DMF in sequence, and add 16g (0.09mol) of 5-oxo-1- Hexyl bromide, after the addition, the mixture was in N 2 Under protection, heat to 120-125°C for 30 minutes, TLC identification of the reaction end point (developing solvent: ethyl acetate: ethanol: glacial acetic acid = 5: 2; 0.1, v: v: v), after the reaction is complete, add 50ml of distilled water, stirred, and then extracted with 200ml×3 chloroform, discarded the aqueous phase, and dried the organic layer with anhydrous sodium sulfate. Filter, concentrate to dryness, and recrystallize the residue with absolute ethanol to obtain 29.5g white crystalli...

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Abstract

The invention discloses a pentoxifylline derivative shown as the formula (1) or pharmaceutically acceptable salt, solvate, optical isomer or polymorph and a pharmaceutical composition containing the compounds, wherein R represents straight chain or branch chain C1-C5 alkyl, C3-C6 naphthenic base or C4-C8 naphthenic alkyl. The invention also discloses a preparation method of the pentoxifylline derivative and application in preparing a medicament with nerve protection function. The compound has favorable effects of hemangiectasis and nerve protection and higher application value in the field ofmedicines.

Description

1. Technical field [0001] The invention relates to a medicinal compound and its preparation method and application, in particular to a new pentoxifylline derivative and its preparation method and application, especially for treating or preventing cerebrovascular diseases. 2. Background technology [0002] Postischemic neuronal cell death and its resulting fatal loss of function, with its corresponding severe neurological and / or psychiatric symptoms, are common clinical features of most cerebrovascular diseases. These include, for example, stroke, transient ischemic attack, multi-infarct dementia, mixed vascular and degenerative (Alzheimer's disease) dementia, spinal cord injury, and brain trauma due to head injury, among others. [0003] In clinical practice, stroke (also known as cerebrovascular accident or cerebral apoplexy) is the mainstream, and it is the main cause of 15% of all deaths, so it ranks third in the cause of death statistics, second only to heart disease and...

Claims

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Application Information

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IPC IPC(8): C07D473/04A61K31/522A61P9/10A61P25/00A61P25/28
Inventor 徐奎
Owner 徐奎
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