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Substituted miazines compound

A technology of compounds and substituents, applied in the field of medicine, can solve problems such as life-threatening, long half-life, and low blood pressure

Inactive Publication Date: 2012-03-14
SHANDONG XUANZHU PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tadalafil has good selectivity to PDE-6, but it has a certain inhibitory effect on PDE-11. Although the clinical pharmacological effects of PDE-11 are unknown, there are still potential risks. There are reports in the literature that tadalafil Non can cause low back pain, whether this is related to PDE-11 still needs to be verified
In addition, the half-life of tadalafil is very long, which can easily cause drug interactions in patients while taking other drugs. danger to life
At present, the pharmacological activity of PDE-5 inhibitors is not satisfactory

Method used

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  • Substituted miazines compound
  • Substituted miazines compound
  • Substituted miazines compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0176] The preparation of embodiment 1 3-chloro-4-methoxybenzylamine

[0177]

[0178] (1) Preparation of 3-chloro-4-methoxybenzyl alcohol

[0179]

[0180] Dissolve methyl 3-chloro-4-methoxybenzoate (1 g, 5 mmol) in 30 mL of dry THF, and slowly add LiAlH at -10 to -20 °C 4 (0.38g, 10mmol), monitored by TLC, after 2 hours of reaction, quenched with 4-5% NaOH solution, added 500mL ethyl acetate, there was a milky precipitate, suction filtered, and rotary evaporated to obtain 3-chloro-4-methoxy 0.78 g of benzyl alcohol, yield 91%.

[0181] (2) Preparation of 4-azidomethyl-2-chloromethoxybenzene

[0182]

[0183] 3-Chloro-4-methoxybenzyl alcohol (200mg, 1.16mmol) was dissolved in 20mL of dry THF, and DBU (210mg, 1.28mmol) and DPPA (320mg, 1.16mmol) were added slowly at 0°C, TLC After about 3 hours of reaction, stop the reaction, add an appropriate amount of saturated NaCl solution, extract with ethyl acetate, rotary evaporate, and pass through the column to obtain 1...

Embodiment 2

[0187] Example 2 (S)-4-(3-chloro-4-methoxybenzylamino)-2-[2-(hydroxymethyl)tetrahydropyrrol-1-yl]-6-methyl-N- Preparation of (pyrimidine-2-methyl)pyrimidine-5-acetamide (compound 1)

[0188]

[0189] (1) Preparation of ethyl 4-(3-chloro-4-methoxybenzylamino)-6-methyl-2-(methylmercapto)pyrimidine-5-carboxylate

[0190]

[0191] Dissolve ethyl 4-chloro-6-methyl-2-(methylmercapto)pyrimidine-5-carboxylate (700mg, 2.8mmol), triethylamine (2mL) in 50mL of anhydrous tetrahydrofuran, add slowly under ice-cooling 3-Chloro-4-methoxybenzylamine (486mg, 2.8mmol), stirred at room temperature for 12 hours, concentrated the reaction solution, added ethyl acetate for extraction, concentrated to give brown solid 4-(3-chloro-4-methoxy Benzylamino)-6-methyl-2-(methylmercapto)pyrimidine-5-carboxylic acid ethyl ester 970 mg, yield 91%.

[0192] (2) Preparation of 4-(3-chloro-4-methoxybenzylamino)-6-methyl-2-(methylmercapto)pyrimidine-5-carboxylic acid

[0193]

[0194] Dissolve ethyl 4...

Embodiment 3

[0206] Example 3 (S)-4-(3-chloro-4-methoxybenzamide)-2-[2-(hydroxymethyl)tetrahydropyrrol-1-yl]-N-(pyrimidine-2- Preparation of methyl) pyrimidine-5-acetamide (compound 2)

[0207]

[0208] (1) Preparation of 4-(3-chloro-4-methoxybenzamide)-2-(methylmercapto)pyrimidine-5-carboxylic acid

[0209]

[0210] 3-Chloro-4-methoxybenzoyl chloride (1.86g, 9mmol) was dissolved in pyridine, and 4-amino-2-(methylmercapto)pyrimidine-5-carboxylic acid (1.67g, 9mmol) was weighed and added to pyridine solution, stirred and heated at 90°C, reacted for 18 hours, returned to room temperature, poured into dilute hydrochloric acid, extracted with dichloromethane, dried over anhydrous sodium sulfate, and spin-dried until a precipitate was precipitated, and the off-white solid 4-(3-chloro -4-methoxybenzamide)-2-(methylmercapto)pyrimidine-5-carboxylic acid 200 mg, yield 6.3%.

[0211] (2) Preparation of 4-(3-chloro-4-methoxybenzamide)-2-(methylmercapto)-N-(pyrimidine-2-methyl)pyrimidine-5-a...

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Abstract

The invention belongs to the technical field of medicine, particularly relates to a substituted miazines compound disclosed in a general formula (I) and clinically-acceptable salt thereof, wherein R1, R2, R3, R4, R5, Z or W is defined as in a specification. The invention also relates to a preparation method of the compounds and the application of the compounds in preparing medicines capable of treating and / or preventing sexual dysfunctions.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to substituted pyrimidine compounds or pharmaceutically acceptable salts thereof, preparation methods of these compounds, and use of these compounds in preparing medicines for treating and / or preventing sexual dysfunction diseases. 2. Background technology [0002] ED (Erectile dysfunction, erectile dysfunction) is the most common sexual dysfunction in adult men, which refers to a disease in which the penis continues to fail to achieve or maintain an erection to satisfy sexual life. ED is divided into organic ED, psychological ED and mixed ED. Organic ED can be subdivided into vascular, neurological, surgical and traumatic, and endocrine. ED is not fatal, but it can reduce a person's quality of life. [0003] Various factors such as cardiovascular disease, diabetes, vascular disease, kidney disease, neurological disease, endocrine disease and psychological factors c...

Claims

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Application Information

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IPC IPC(8): C07D403/14A61K31/506A61P15/10
Inventor 黄振华
Owner SHANDONG XUANZHU PHARMA TECH CO LTD
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