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Tanshinone IIA derivatives and pharmaceutical application thereof

A derivative, tanshinone technology, applied in the field of medicine, can solve the problems of low pH value, high product irritation, failure to fully exert the medicinal value and social value of tanshinone IIA, and achieve the effect of increasing drug efficacy

Active Publication Date: 2006-09-27
JIANGSU CAREFREE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] But prove through a large amount of pharmacology and clinical use, tanshinone II A sodium sulfonate has a strong acidic group, makes injection, and pH value is low, and acidity is strong, causes product irritation big, during clinical use, brings certain effect to patient. pain of
[0007] For more than 20 years, the only water-soluble derivative of tanshinone II A is sodium tanshinone II A sulfonate, which has not fully utilized the medicinal and social value of tanshinone II A

Method used

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  • Tanshinone IIA derivatives and pharmaceutical application thereof
  • Tanshinone IIA derivatives and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1. 2-(diallylamine) methyl-tanshinone II A synthesis steps and structural confirmation

[0053] Mix 1.56g of tanshinone, 0.5mL of 37% formaldehyde solution, 2.4g of diallylamine, and 50mL of acetic acid, heat and reflux in an oil bath for 5h, remove the solvent from the mixture under reduced pressure to obtain a red solid, dissolve it in water, filter, and adjust the filtrate with alkali pH to 9, filtered, the filter cake was dried, and separated by silica gel column chromatography (eluent: chloroform / methanol=15 / 1) to obtain 1.15 g (yield 53%) of the expected compound.

[0054] 1 H-NMR (CDCl 3)δ7.71(d, 1H), 7.66(d, 1H), 5.31~5.45(m, 2H), 4.65~4.81(m, 4H), 3.50(s, 2H), 3.15(m, 2H), 2.55 ~2.71(m, 4H), 2.18(s, 6H), 2.07(s, 3H), 1.74(m, 2H), 1.61(m, 2H).

Embodiment 2

[0055] Example 2. Synthesis steps and structural confirmation of 2-(sodium iminodiacetate) methyl-tanshinone II A

[0056] Mix 1.56g of tanshinone, 0.5mL of 37% formaldehyde solution, 4.2g of iminodiacetic acid hydrochloride, and 50mL of acetic acid, heat and reflux in an oil bath for 5h, remove the solvent from the mixture under reduced pressure to obtain a red solid, dissolve in water, filter, and filtrate Add alkali to adjust the pH to 9, filter, dry the filter cake, and separate by silica gel column chromatography (eluent: chloroform / methanol=15 / 1) to obtain 1.41 g (yield 60%) of 2-iminodiacetic acid-tanshinone II A, and then dissolved in twice the molar amount of sodium bicarbonate solution, filtered to remove insoluble matter, and the filtrate was dried to obtain the desired compound.

[0057] 1 H-NMR (CDCl3) δ7.62(d, 1H), 7.56(d, 1H), 3.64(s, 2H), 3.35~3.51(m, 4H), 3.15(m, 2H), 2.09(s, 6H) ), 1.95(s, 3H), 1.75(m, 2H), 1.61(m, 2H).

Embodiment 3

[0058] Example 3. 2-(cyclohexylamine) methyl-tanshinone II A synthesis steps and structure confirmation

[0059] Mix 1.56g of tanshinone, 0.5mL of 37% formaldehyde solution, 2.5g of cyclohexylamine, and 50mL of acetic acid, heat and reflux in an oil bath for 5 hours, remove the solvent from the mixture under reduced pressure to obtain a red solid, dissolve it in water, filter, and adjust the pH of the filtrate to 9. Filter, dry the filter cake, and separate by silica gel column chromatography (eluent: chloroform / methanol=15 / 1) to obtain 1.41 g (yield 60%) of the expected compound.

[0060] 1 H-NMR (CDCl3) δ7.68(d, 1H), 7.52(d, 1H), 3.55(s, 2H), 3.21~3.32(m, 4H), 3.13(m, 2H), 2.12(s, 6H) ), 2.03(s, 3H), 1.75(m, 2H), 1.62(m, 2H), 1.52~1.61(m, 4H), 1.32~1.41(m, 4H).

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Abstract

The invention discloses a tanshinone IIA derivant and application in pharmacy, which is characterized by the following: the derivant constitutional formula is showed in the right chart; when R1 represents -Ar, R2,R3 represents hydrogen or alkyl with one to eight carbon atoms; or R2-N-R3 represents saturated heterocycle with nitrogen, imidazoline and its derivant, glyoxaline and its derivant, diethylenediamine and its derivant, piperidine and its derivant, morpholine and its derivant; when R1 represents -H, R2,R3 represents alkyl with three to eight carbon atoms, cycloalkyl and aromatic nucleus; or R2-N-R3 represents cyclohexylamine, imidazoline and its derivant, glyoxaline and its derivant, piperazine, piperazine and derivant of derivant. The derivant can improve the bioavailability of original chemical compoundm.

Description

technical field [0001] The invention relates to a class of compound derivatives and their application in pharmacy, in particular to derivatives of tanshinone II A and their application in pharmacy, belonging to the technical field of medicine. Background technique [0002] Salvia miltiorrhiza is the dry root and rhizome of Salvia miltiorrhiza Bge., a plant in the Labiatae family. It was first recorded in "Shen Nong's Materia Medica", and has been recorded in successive dynasties of herbal medicines. It is bitter in taste, slightly cold in nature, and enters the two meridians of Guixin and Liver. Tool dispelling blood stasis and relieving pain, promoting blood circulation to stimulate menstrual flow, clearing away heart-fire and eliminating troubles. Salvia miltiorrhiza is a traditional Chinese medicine for promoting blood circulation and removing blood stasis, and its commonly used preparations are mainly used to treat cardiovascular and cerebrovascular diseases. The chemi...

Claims

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Application Information

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IPC IPC(8): C07D307/81A61K31/343A61K9/08A61K9/14A61K9/20A61K9/48
Inventor 秦引林
Owner JIANGSU CAREFREE PHARM CO LTD
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