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CDDO ethyl ester polymorphic substance and application thereof

A technology of polymorphism and polymorphism, which is applied in the direction of medical preparations containing active ingredients, drug combinations, steroids, etc., and can solve problems such as weak biological activity

Active Publication Date: 2014-04-30
APPLIED PHARMA SCI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although triterpenoids are candidate drug compounds, these naturally occurring molecules exhibit relatively weak biological activity

Method used

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  • CDDO ethyl ester polymorphic substance and application thereof
  • CDDO ethyl ester polymorphic substance and application thereof
  • CDDO ethyl ester polymorphic substance and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1. Synthesis of the compound of formula I

[0063]

[0064] Step 1 Synthesis of APSN13B-1

[0065] name

M.W.

the amount

mol

equivalent

Oleanolic acid

456

1000g

2.2mol

1

EtI

156

376g

2.4mol

1.1

K 2 CO 3

138

604g

4.4mol

2

DMF

/

12L

/

/

[0066] To a solution of oleanolic acid (1000g, 2.2mol) and potassium carbonate (604g, 4.4mol) dissolved in DMF (12L) was added iodoethane (376g, 2.4mol). The resulting mixture was stirred overnight at 45°C. After oleanolic acid could not be detected by HPLC, the mixture was cooled to room temperature and poured into water (120 L). The resulting suspension was stirred for 30 minutes. The solid was collected by a centrifuge, washed with water (1L) and dried in vacuum at 50°C to obtain 976g APSN13B-1 for subsequent steps. The yield is 92%.

[0067] Step 2. Synthesis of APSN13B-2

[0068] name

M.W.

the amount

mol

equivalent

APSN13B-1

484

975g

2mol

1

Ac 2 O

102

612g

6mol

3

Pyridine

79

474g

6mol

3...

Embodiment 2

[0102] Example 2. Preparation of the crystal form of the compound represented by formula I

[0103] The compound of formula I prepared by the method described in Example 1 above is dissolved in heptane solvent at room temperature, and then the desired crystal form I is obtained by natural precipitation, and its melting point is 174-177°C.

[0104] figure 1 The X-ray powder diffraction pattern shown in Table 1 is summarized.

[0105] Table 1

[0106]

Embodiment 3

[0107] Example 3. Preparation of the crystal form II of the compound represented by formula I

[0108] The compound represented by the formula I prepared by the method described in the above-mentioned embodiment 1, the excess of the compound is added to the mixed solvent of ethyl acetate and heptane (the ratio of ethyl acetate and heptane is 1:10, the weight ratio or volume Compared with), stir to make the slurry, and stir at room temperature or 50°C for at least 48 hours to obtain crystal form II with a melting point of 209-212°C.

[0109] figure 2 The X-ray powder diffraction pattern shown in Table 2 is summarized.

[0110] Table 2

[0111]

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Abstract

The invention relates to a polymorphism shape of a compound disclosed as Formula I (ethyl 2-cyano-3,12-dioxooleanane-1,9(11)diolefin-28-ester (CDDO ethyl ester)) and a method thereof for treating various diseases, such as cancers and inflammation accompanied by the cancers.

Description

[0001] Cross-reference related applications [0002] This application claims the priority of the PCT international application with the international application number PCT / CN2012 / 082278 filed on September 28, 2012, and the entire content of the earlier application is hereby incorporated by reference. Technical field [0003] This application relates to the polymorphic form of a triterpene compound, ethyl 2-cyano-3,12-dioxoolean-1,9(11) diene-28-ester (CDDO ethyl ester) , And using at least one of their polymorphic forms to treat various disease states, generally a method of disease states related to inflammation. Background technique [0004] Triterpenoids are biosynthesized through the cyclization reaction of squalene in plants. Although triterpenoids are candidate drug compounds, these naturally-occurring molecules show relatively weak biological activity. Therefore, chemists have tried to synthesize similar compounds with improved potency (Honda et al., 1997 and 1998). [0005]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P35/00A61P29/00A61P19/02A61P1/00A61P9/00A61P3/10A61P3/04A61P9/12A61P9/10A61P13/12A61P25/00A61P21/00A61P27/02A61P3/00A61P43/00
Inventor 张晓红律嵩孙文东刘锎扬韩春磊
Owner APPLIED PHARMA SCI
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