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Co-crystal of tofu glucoside and L-proline and preparation method thereof

A technology of proline and co-crystal crystal form, which is applied to the co-crystal of tofufuside and L-proline and the field of preparation thereof, can solve problems such as few reports, and achieves convenient long-term storage, improved absorption efficiency, stable good effect

Active Publication Date: 2018-08-10
CRYSTAL PHARMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the process of researching tofu fruit glucoside preparations, it is necessary to control the crystal form of tofu fruit glucoside, but there are few related research reports at home and abroad

Method used

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  • Co-crystal of tofu glucoside and L-proline and preparation method thereof
  • Co-crystal of tofu glucoside and L-proline and preparation method thereof
  • Co-crystal of tofu glucoside and L-proline and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] The preparation method of the co-crystal form A of the compound of formula (I) and L-proline:

[0063] Add 185.2 mg of the compound of formula (I) to 10.0 mL of 1,4-dioxane to obtain a suspension, add 76.6 mg of L-proline and place it in a constant temperature incubator at 50°C for 24 hours, then centrifuge to remove the lower layer The solid was dried at a constant temperature at 25°C overnight, and the obtained solid was co-crystal form A.

[0064] Table 1 shows the X-ray powder diffraction data of the crystal forms obtained in this example. Its XRPD pattern is as follows figure 1 , and its DSC graph is shown in figure 2 , and its TGA figure is shown in image 3 ,That 1 H NMR picture as Figure 7 .

[0065] The product of the eutectic crystal form A prepared by the above method, which 1 H NMR identification data are as follows:

[0066] 1 H-NMR (400 MHz, DMSO-d 6 )δ9.89(s,1H),7.87(d,J=8.7Hz,2H),7.18(d,J=8.7Hz,2H),5.25(d,J=7.9Hz,1H),4.90-5.20( m, 2H), 4.38-...

Embodiment 2

[0070] The preparation method of the co-crystal form A of the compound of formula (I) and L-proline:

[0071] Add 15.0 mg of the compound of formula (I) to 1.0 mL of 1,4-dioxane to obtain a suspension, add 6.0 mg of L-proline, place in a constant temperature incubator at 50°C and stir for 24 hours, centrifuge to take the lower layer of solid , 25 ° C constant temperature drying overnight, the resulting solid is the eutectic crystal form A.

[0072] The X-ray powder diffraction data of the crystal forms obtained in this example are shown in Table 2.

[0073] Table 2

[0074] 2theta

Embodiment 3

[0076] The preparation method of the co-crystal form B of the compound of formula (I) and L-proline:

[0077] Add 99.6 mg of co-crystal form A to 4.0 mL of tetrahydrofuran to obtain a suspension, place the suspension in a constant temperature incubator at 50°C and stir for 24 hours, centrifuge to remove the lower layer of solid, and dry at a constant temperature of 25°C overnight, the obtained solid is Eutectic Form B.

[0078] The X-ray powder diffraction data of the crystal forms obtained in this example are shown in Table 3. Its XRPD pattern is as follows Figure 4 , and its DSC graph is shown in Figure 5 , and its TGA figure is shown in Figure 6 , whose H 1 -NMR picture as Figure 8 .

[0079] The product of the eutectic crystal form B prepared by the above method, which 1 H NMR identification data are as follows:

[0080] 1 H-NMR (400 MHz, DMSO-d 6 )δ9.90(s,1H),7.88(d,J=8.7Hz,2H),7.19(d,J=8.7Hz,2H),5.26(d,J=7.9Hz,1H),4.90-5.21( m, 2H), 4.43-4.78(m, 2H), 3.95(...

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Abstract

The invention relates to eutectic crystals of Helicid and L-proline and preparation methods thereof. Specifically, the eutectic crystals provided by the invention are named as an eutectic crystal type A and an eutectic crystal type B. The eutectic crystals provided by the invention have good stability, low hygroscopicity and higher solubility, and have important values for optimization and development of future medicines.

Description

technical field [0001] The invention relates to the field of chemistry and medicine, in particular to a co-crystal of tofu fruit glycoside and L-proline and a preparation method thereof. Background technique [0002] Tofu fruit glycoside (Helicid), also known as Shenshouguo element, is an active ingredient extracted from the fruit of the radish tree of the genus Longan. Its chemical name is p-formaldehyde phenyl O-β-D-alupyranoside, and tofu Glycoside is a substance with sedative and hypnotic activity, and has obvious therapeutic effect on sleep disorders, anxiety and depression. Its analgesic, hypnotic and analgesic effects are stronger than those of gastrodin, and it has a certain curative effect on the treatment of neurosis and has no side effects such as rebound insomnia and drug dependence, so it has good clinical use value. Its structure is shown in formula (I): [0003] [0004] At present, there are many studies on tofu fruit glycosides, and there are many paten...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/203C07H1/06C07D207/16A61K31/7034A61P25/04A61P25/06A61P25/20
Inventor 陈敏华张炎锋刁小娟张晓宇
Owner CRYSTAL PHARMATECH CO LTD
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