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Use of tetrahydroisoquinoline derivatives

A tetrahydroisoquinoline, a technology for use, applied in the field of natural medicine and medicinal chemistry, can solve the problems of loss of response to harmful stimuli, burning sensation, loss of pain sensation, etc.

Inactive Publication Date: 2010-08-04
CHINA PHARM UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of capsaicin can produce some side effects, such as a burning sensation when applied topically, loss of pain sensation after a few days to a few weeks, and loss of response to various harmful stimuli

Method used

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  • Use of tetrahydroisoquinoline derivatives
  • Use of tetrahydroisoquinoline derivatives
  • Use of tetrahydroisoquinoline derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Preparation of 6,7-dimethoxytetrahydroisoquinoline (2)

[0065] Add 10 g of 3,4-dimethoxyphenethylamine and 4.6 g of formaldehyde aqueous solution into a 50 ml round bottom bottle, heat to 100° C., and keep it warm for half an hour. The reaction solution was divided into two layers, part of the upper aqueous solution was sucked off with a dropper, about 29.7 ml of 23% HCl was added, and stirred to obtain a brownish-yellow clear solution. The water was distilled off under reduced pressure to obtain a brown-yellow viscous solid, which was recrystallized with 95% ethanol to obtain 9.07 g of white crystals. Put the solid into a beaker, add ammonia water, adjust the pH to 9-10, add water, extract 3 times with chloroform, combine the chloroform layers, wash with saturated sodium chloride, anhydrous MgSO 4 dry. The liquid was filtered off and evaporated to dryness to obtain 7.62g of a light yellow solid with a yield of 71.8%, mp: 135-137°C

Embodiment 2

[0067] Preparation of isothiocyanates (4a-i)

[0068] 1.07ml (10mmol) of o-toluene was dissolved in 7ml of toluene, and 0.6ml of CS was added 2 And 1.4ml of triethylamine, heated to 35-40 ℃ for 6h, a light yellow solid appeared, filtered out the solid, washed with a small amount of toluene. The solid was dissolved in 10ml CHCl 3 , add 1.4ml triethylamine, cool in ice bath to below 0℃, add dropwise 0.78ml ClCOOCH 3 / 3mlCHCl 3 solution. React at room temperature for 5 hours, add 3ml 1N HCl, stir for 10 minutes, pour the reaction solution into a separatory funnel, and separate the CHCl 3 layer, washed with water to neutral, anhydrous Na 2 SO 4 dry. The solid was filtered out, and the filtrate was subjected to column chromatography (PE was the eluent) to obtain a colorless liquid, which was o-methylphenyl isothiocyanate 4a.

[0069] The same method makes p-methylphenyl isothiocyanate (4b), p-methoxyphenyl isothiocyanate (4c), m-methoxyphenyl isothiocyanate (4d), o- Methox...

Embodiment 3

[0071] 6,7-dimethoxy-2-[N-(2-methylphenyl)]thioureido-1,2,3,4-tetrahydroisoquinoline (I 1 ) preparation

[0072] Add 20ml of absolute ethanol and 0.27ml (2mmol) o-methylphenyl isothiocyanate (4a) to 0.39g (2mmol) of 2, and reflux until the reaction is complete. The reaction solution was left to cool down, and solids precipitated out. The solids were filtered out, washed with absolute ethanol, and dried to obtain 0.42 g of white solids, yield 61.4%, mp: 143-145°C

[0073] IR (KBr, cm -1 ): 3241 (v NH ), 3010(v φH ), 1611 (v C＝C ), 1517 (v C＝S ), 1493, 1474 (aromatic), 1322, 1180, 731

[0074] 1 HNMR (CDCl 3 , 300Hz): δ7.13-7.27 (m, 4H, Ar-H), δ6.96 (bs, 1H, NH), δ6.61-6.68 (d, 2H, Ar-H), δ4.85 (s , 2H, ArCH 2 N), δ3.99(t, 2H, ArCH 2 C H 2 N), δ3.86(d, 6H, OCH 3 , OCH 3 ), δ2.88(t, 2H, ArC H 2 CH 2 N), δ2.29(s, 3H, CH 3 )

[0075] MS (ESI, m / z): 343.2 (M+H + , base peak)

[0076] Anal.Calcd.for C 19 h 22 N 2 SO 2 : C 66.67, H 6.43, N 8.19; Found C 66.48...

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PUM

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Abstract

The invention relates to the use of tetrahydroisoquinoline derivatives and relates to the use of compounds of a general formula (1) and salts thereof in the preparation of medicaments, in particular to the use in the preparation of novel anti-inflammatory and analgesic medicaments. The tetrahydroisoquinoline derivatives have the same or higher activity than ibuprofen and avoid gastrointestinal tract side effects of common nonsteroidal anti-inflammatory medicaments.

Description

technical field [0001] The invention relates to the fields of natural medicine and medicinal chemistry, in particular to a class of tetrahydroisoquinoline derivatives, and their use in the preparation of medicines, in particular to the preparation of novel analgesic medicines. Background technique [0002] Pain, especially chronic pain, has always been a persistent disease that plagues human health. Due to the complexity of the pathological mechanism, the drugs for the treatment of pain have certain limitations at present, and the development of analgesic drugs with high efficiency and low toxicity has always been one of the hot spots in the research of new drugs. [0003] There are two main classes of analgesic drugs most commonly used today: opioids and nonsteroidal anti-inflammatory drugs (NSAIDs). [0004] Opioid analgesics produce analgesic effect by binding to opioid receptors and activating opioid receptors. These drugs usually work quickly and can significantly red...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/472A61P29/00
Inventor 黄文龙张惠斌钱海周金培张晓燕戴冬艳沈竞康
Owner CHINA PHARM UNIV
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