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Tanshinon IIA crylic acid or sodium salt thereof, preparation method and application thereof

A technology of sodium acrylate and tanshinone, which is applied in the fields of organic chemical synthesis and medicine, can solve the problems such as failure to give full play to the medicinal value and social value of tanshinone IIA, achieve enhanced bioavailability and curative effect, improved bioavailability and curative effect, The effect of improving water solubility

Active Publication Date: 2011-02-16
JIANGSU CAREFREE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] 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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  • Tanshinon IIA crylic acid or sodium salt thereof, preparation method and application thereof
  • Tanshinon IIA crylic acid or sodium salt thereof, preparation method and application thereof
  • Tanshinon IIA crylic acid or sodium salt thereof, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1, the synthesis of tanshinone IIA sodium acrylate:

[0043]

[0044] (1). Synthesis of tanshinone II A formaldehyde: 7.40g (25.14mmol) of tanshinone II A was dissolved in 150mL of DMF, 20mL of phosphorus oxychloride was added dropwise at room temperature, stirred for 2 hours, and the reaction solution was poured into 2000mL of ice water to obtain A yellow solid was precipitated, filtered, and the filter cake was washed with water until neutral, dried, and the yield was quantitative.

[0045] (2). Synthesis of tanshinone II A acrylic acid: 500 mg (1.55 mmol) of tanshinone II A formaldehyde was dissolved in 100 mL of benzene, 10 mL of pyridine and 240 mg of malonic acid were added successively, heated to reflux to separate water, and after 10 hours of reaction, evaporated under reduced pressure Solvent, add 50 mL of 5% sodium carbonate aqueous solution to the residue, filter, adjust the pH of the filtrate to nearly 2 with concentrated hydrochloric acid, and...

Embodiment 2

[0047] Embodiment 2, the synthesis of tanshinone IIA sodium formate:

[0048]

[0049] (1). Synthesis of tanshinone IIA formaldehyde: same as above

[0050] (2). Synthesis of tanshinone II A formic acid: 500 mg (1.55 mmol) of tanshinone II A formaldehyde was dissolved in 50 ml of acetone, and 20 mL of 5% potassium permanganate aqueous solution was added dropwise at 0° C., reacted for 10 hours, and removed by filtration Insoluble matter, the filtrate was evaporated under reduced pressure to remove the organic solvent, filtered again, and the pH of the filtrate was adjusted to nearly 2 with concentrated hydrochloric acid, that is, a solid precipitated, filtered and dried to obtain a brown solid

Embodiment 3

[0051] Embodiment 3, the synthesis of tanshinone IIA-2-sodium butenoate

[0052]

[0053] (1). Synthesis of tanshinone II A ethyl ketone: 3.70 g (12.60 mmol) of tanshinone II A was dissolved in 150 ml of pyridine, 10 mL of redistilled acetyl chloride was added dropwise at room temperature, stirred for 2 hours, and the reaction solution was poured into 2000 mL of ice water, namely A yellow solid precipitated, filtered, washed the filter cake until neutral, dried to obtain tanshinone IIA ethyl ketone.

[0054] (2). Synthesis of tanshinone II A-2-butenoic acid: Dissolve 500mg of tanshinone II A ethyl ketone in 100mL of benzene, add 10mL of pyridine and 240mg of malonic acid in turn, heat and reflux to separate water, react for 10 hours, and depressurize The solvent was evaporated, and 50 mL of 5% sodium carbonate aqueous solution was added to the residue, filtered, and the pH of the filtrate was adjusted to nearly 2 with concentrated hydrochloric acid, and a solid was precipit...

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Abstract

The invention discloses a tanshinon IIA crylic acid or sodium salt thereof, a preparation method and application thereof. The tanshinon IIA crylic acid or sodium salt thereof has the following structure described in the specification. The tanshinon IIA crylic acid or sodium salt thereof provides a reliable path for the clinical application of the tanshinon IIA, and makes up the defects of hyperacidity and large stimulation of a sodium tanshinon II asilate injection as a clinical medicament.

Description

[0001] This application is a divisional application for an invention patent with the application date of October 25, 2005, the application number 200510095006.2, and the name is a class of tanshinone IIA derivatives and their application in pharmacy. technical field [0002] The invention relates to a derivative of tanshinone II A and its application in pharmacy, belonging to the technical fields of organic chemical synthesis and medicine. Background technique [0003] 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 tra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P19/08A61P9/06A61P9/00A61P1/16A61P17/02A61P31/12A61K31/58A61P35/00A61P27/02C07J73/00A61P9/12A61P13/12A61P15/00A61P11/00A61P7/02A61P1/02A61P11/06A61P9/10
Inventor 秦引林夏鹏张倩陈瑛
Owner JIANGSU CAREFREE PHARM CO LTD
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