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Recrystallization method of andrographolide C15-substituted derivative

A technology of andrographolide and derivatives, applied in the direction of organic chemistry and the like, can solve problems such as large amount of solvent, and achieve the effects of stable product quality, convenient operation and saving production cost

Pending Publication Date: 2021-08-17
SHIJIAZHUANG NO 4 PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the problem that the amount of solvent used in the recrystallization process of 15Z)15-(4-chlorophenyl)-methylene-11,12-dehydro-14-deoxyandrographolide is very large at present, the present invention provides a Recrystallization method of derivatives substituted at C15 position of andrographolide

Method used

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  • Recrystallization method of andrographolide C15-substituted derivative
  • Recrystallization method of andrographolide C15-substituted derivative
  • Recrystallization method of andrographolide C15-substituted derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0033] This example provides a recrystallization method of 15Z)15-(4-chlorophenyl)-methylene-11,12-dehydro-14-deoxyandrographolide.

[0034] Step a, add 14.85L (9vol) tetrahydrofuran to a 20L glass reactor, and add 1.65kg 15Z)15-(4-chlorophenyl)-methylene-11,12-dehydro-14-deoxyandrographis paniculata while stirring For the crude ester (content 80.3%), turn on the heating and heat up to reflux until the material is completely dissolved, add 132g of activated carbon, heat filter to remove carbon after reflux for 15min, transfer the filtrate to another 20L glass reactor, stir slowly and cool down to 0 Crystallization at ~5°C. Centrifuge and dry at 65° C. for 10 hours to obtain 866.2 g of the light yellow first solid, with a content of 99.91%, a purity of 99.73%, and a yield of 65.4%. The centrifuged mother liquor is transferred to a 100L glass-lined reaction tank for recovery. Wherein yield=first solid mass×first solid content / (crude product mass×crude product content)×100%.

...

Embodiment 2

[0038] This example provides a recrystallization method of 15Z)15-(4-chlorophenyl)-methylene-11,12-dehydro-14-deoxyandrographolide.

[0039] Step a, add 9.75L (6.5vol) tetrahydrofuran to a 20L glass reactor, and add 1.50kg15Z)15-(4-chlorophenyl)-methylene-11,12-dehydro-14-deoxyandrographis paniculata while stirring For the crude ester (content 78.9%), turn on the heating and heat up to reflux until the material is completely dissolved, add 90.0g of activated carbon, heat filter to remove carbon after reflux for 60min, transfer the filtrate to another 20L glass reactor, stir slowly and cool down to Crystallization at 0~5℃. Centrifuge and dry at 65° C. for 10 hours to obtain 840 g of the light yellow first solid, with a content of 99.97%, a purity of 99.68%, and a yield of 71.0%. The centrifuged mother liquor is transferred to a 100L glass-lined reaction tank for recovery. Wherein yield=first solid mass×first solid content / (crude product mass×crude product content)×100%.

[00...

Embodiment 3

[0043] This example provides a recrystallization method of 15Z)15-(4-chlorophenyl)-methylene-11,12-dehydro-14-deoxyandrographolide.

[0044] Step a, add 14.0L (8vol) THF to a 20L glass reactor, and add 1.75kg15Z)15-(4-chlorophenyl)-methylene-11,12-dehydro-14-deoxyandrographolide under stirring Crude product (content 77.2%), turn on heating and heat up to reflux until the material is completely dissolved, add 87.5g of activated carbon, heat filter to remove carbon after reflux for 45min, transfer the filtrate to another 20L glass reactor, stir slowly and cool down to 0 Crystallization at ~5°C. After centrifugation and air drying at 65° C. for 10 h, 920 g of the light yellow-green first solid was obtained, with a content of 99.94%, a purity of 99.71%, and a yield of 68.1%. ; The centrifuged mother liquor is transferred to a 100L glass-lined reaction tank to be recovered. Wherein yield=first solid mass×first solid content / (crude product mass×crude product content)×100%.

[004...

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Abstract

The invention relates to the technical field of medicinal chemistry, in particular to a recrystallization method of an andrographolide C15-substituted derivative. The andrographolide C15-substituted derivative is 15Z) 15-(4-chlorphenyl)-methylene-11, 12-dehydro-14-deoxy andrographolide. The method comprises the following steps: carrying out recrystallization on a crude product of the 15Z) 15-(4-chlorphenyl)-methylene-11, 12-dehydro-14-deoxy andrographolide by using tetrahydrofuran, and carrying out crystal transformation by using a crystal transformation solvent to obtain a stable crystal form. According to the method, the amount of the solvent required to be used in the crystallization process is effectively reduced, and the unit operation efficiency can be improved; the solvent is easy to recover and the cost can be reduced; and the method is simple in process, convenient to operate, mild in condition and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a recrystallization method of a C15-position substituted derivative of andrographolide. Background technique [0002] For drugs with the same chemical structure, different crystal forms can be obtained due to different crystallization conditions. Some are stable forms, some are metastable forms, and metastable forms may eventually transform into stable forms. Although compounds with different crystal forms have the same chemical quality, their physical and chemical properties may be different. Under a certain temperature and pressure, the drug with stable crystal form has the smallest entropy value, the highest melting point, low solubility and good chemical stability, while the metastable drug has high entropy value, low melting point, high solubility and fast dissolution rate. . Therefore, drugs with the same chemical structure may exhibit different so...

Claims

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Application Information

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IPC IPC(8): C07D307/58
CPCC07D307/58
Inventor 孙立杰单振际朱树杰印杰魏赛丽张娜郭凯刘杰
Owner SHIJIAZHUANG NO 4 PHARMA
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