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Co-crystal of oleanolic acid and choline, its preparation method and its pharmaceutical composition

A technology of oleanolic acid and composition, applied in the field of new crystal compounds

Active Publication Date: 2019-07-05
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] So far, there are no reports describing the formation of salts or co-crystals of oleanolic acid and choline

Method used

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  • Co-crystal of oleanolic acid and choline, its preparation method and its pharmaceutical composition
  • Co-crystal of oleanolic acid and choline, its preparation method and its pharmaceutical composition
  • Co-crystal of oleanolic acid and choline, its preparation method and its pharmaceutical composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Preparation of Oleanolic Acid / Choline / Isopropanol 2:1:1 Cocrystal A

[0071] 0.54 g of choline aqueous solution (49%, choline content 0.27 g) was dissolved in 50 mL of isopropanol, and the solution was pale yellow. Under heating (80°C), 2.0 g of oleanolic acid was added, stirred until the solution was clear, and continued stirring for about 0.5 h. Turn off the heat, slowly cool to room temperature, and let stand. White needle-like crystals were precipitated, filtered by suction, and dried to obtain 1.58 g of a white solid, namely oleanolic acid / choline / isopropanol 2:1:1 cocrystal A: 1 H NMR (DMSO, 300MHz) δ5.07(s, 2H), 3.84(m, 2H), 3.77(m, 1H), 3.41(m, 2H), 3.12(s, 9H), 2.99(m, 2H) , 2.78(m, 2H), 1.70-1.85(m, 8H), 1.20-1.60(m, 27H), 1.00-1.10(m, 16H), 0.80-0.95(m, 27H), 0.65-0.75(m, 14H).

Embodiment 2

[0073] Preparation of Oleanolic Acid / Choline / Isopropanol 2:1:1 Cocrystal A

[0074] Under heating (80°C), 1.20 g of oleanolic acid was dissolved in 85 mL of ethyl acetate, and the solution was clear. Slowly add 0.65 g of choline aqueous solution (49%, choline content 0.32 g) dropwise under stirring, the reaction solution gradually becomes turbid, and finally forms a milky white suspension. Heating was stopped, cooled to room temperature, and a white solid was obtained by suction filtration. The resulting white solid was recrystallized from isopropanol to obtain oleanolic acid / choline / isopropanol 2:1:1 co-crystal A (1.25 g).

Embodiment 3

[0076] Preparation of Oleanolic Acid / Choline 2∶1 Cocrystal B

[0077] The oleanolic acid / choline / isopropanol 2:1:1 eutectic A (1.52g) prepared in Example 1 was heated (150° C.) under normal pressure and dried for 1 hour to obtain the olean fruit Acid / choline 2:1 cocrystal B (1.40 g): 1 H NMR (DMSO, 300MHz) δ5.05(s, 2H), 3.82(m, 2H), 3.40(m, 2H), 3.10(s, 9H), 2.98(m, 2H), 2.78(m, 2H) , 1.70-1.85(m, 8H), 1.20-1.60(m, 27H), 1.00-1.10(m, 9H), 0.80-0.95(m, 26H), 0.65-0.75(m, 13H).

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Abstract

The invention relates to a eutectic crystal of oleanolic acid and choline, in particular to a eutectic crystal B formed by oleanolic acid and choline according to the ratio of 2:1. The eutectic crystal B has the solubility property and medicinal treatment effect which are superior to those of oleanolic acid itself. The invention further provides a preparation method of the eutectic crystal containing oleanolic acid and choline and a pharmaceutical composition containing the eutectic crystal.

Description

technical field [0001] The present invention relates to a novel crystal compound containing oleanolic acid, in particular to a co-crystal formed between oleanolic acid and choline, a preparation method thereof and a pharmaceutical composition containing the same. Background technique [0002] Oleanolic acid tablet is an over-the-counter liver-protecting drug, which is clinically used as an adjuvant treatment of acute and chronic hepatitis, and has a certain protective effect on liver damage. On the other hand, a lot of research work shows that oleanolic acid also has the effects of lowering lipid, lowering blood sugar, anti-tumor, immune regulation, neuroprotection and anti-cardiovascular and cerebrovascular diseases (Natural Product Reports 2011, 28, 543-593) . What is particularly noteworthy is that the inventors have proved that oleanolic acid has a very significant hypolipidemic effect on hyperlipidemia animal models (201210454865.6). At present, oleanolic acid has no ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00C07C215/40A61K31/56A61K31/14A61P3/06A61P9/10A61P3/10A61P35/00A61P1/16A61P25/28A61P13/12A61P29/00A61P19/02
Inventor 孙宏斌林超柳军温小安
Owner CHINA PHARM UNIV
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