Novel crystal form of isotretinoin as well as preparation method and application thereof

A tretinoin and crystal form technology, applied in the crystal form preparation process and application field of isotretinoin, can solve the problems such as the transformation of isotretinoin crystal form that has never been reported, and achieves overcoming poor stability, The effect of convenient industrial production and easy processing

Inactive Publication Date: 2015-03-25
CHONGQING HUAPONT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the preparation method of isotretinoin raw material is very mature, there has never been any report on the modification of the crystal form of isotretinoin

Method used

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  • Novel crystal form of isotretinoin as well as preparation method and application thereof
  • Novel crystal form of isotretinoin as well as preparation method and application thereof
  • Novel crystal form of isotretinoin as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] It is prepared by US4556518 patented technology to obtain the raw material drug of isotretinoin. Under the condition of blowing nitrogen gas, add methanol and the raw material drug of isotretinoin into the reaction bottle, and heat at 50° C. until completely dissolved to obtain an organic alcohol solution of isotretinoin.

[0044] The organic alcohol solution of isotretinoin is crystallized by the temperature difference method, the crystallization temperature is 10°C, the crystallization time is 20 hours, and the solid-liquid separation is carried out by filtration, and the solid is dried at 40°C to obtain isotretinoin A crystal form.

Embodiment 2

[0046] It is prepared by US6177579 patented technology to obtain the raw material drug of isotretinoin. Under the condition of blowing nitrogen gas, add ethanol and the crude drug of isotretinoin into the reaction bottle, and heat at 70° C. until completely dissolved to obtain the organic alcohol solution of isotretinoin.

[0047] The organic alcohol solution of isotretinoin is crystallized by the temperature difference method, the crystallization temperature is -15°C, the crystallization time is 1 hour, and the solid-liquid separation is carried out by filtration, and the solid is dried at 60°C to obtain isotretinoin A Form A of the acid.

Embodiment 3

[0049] It is prepared by US6177579 patented technology to obtain the raw material drug of isotretinoin. Under the condition of blowing nitrogen gas, add butanol and the raw material drug of isotretinoin into the reaction bottle, and heat at 70° C. until completely dissolved to obtain an organic alcohol solution of isotretinoin.

[0050] The organic alcohol solution of isotretinoin is crystallized by the temperature difference method, the crystallization temperature is -15°C, the crystallization time is 1 hour, and the solid-liquid separation is carried out by filtration, and the solid is dried at 60°C to obtain isotretinoin A Form A of the acid.

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Abstract

The invention relates to the field of medicinal chemistry, in particular to a crystal form preparation process and application of isotretinoin. A crystal form A takes positions 2theta of diffraction peaks as spectrogram feature parameters, wherein the positions 2theta sequentially comprise 5.8+/-0.2, 10.52+/-0.2, 11.46+/-0.2, 11.87+/-0.2, 12.56+/-0.2, 15.83+/-0.2, 16.49+/-0.2, 18.11+/-0.2, 19.70+/-0.2, 20.24+/-0.2, 21.68+/-0.2, 24.83+/-0.2, 25.40+/-0.2, 26.94+/-0.2, 28.62+/-0.2, and 30.87+/-0.2. A specific preparation method comprises the steps that an isotretinoin raw material is dissolved with organic alcohol to obtain an isotretinoin organic alcohol solution, crystallization is conducted with a temperature differential method, solid-liquid separation is conducted, a solid is dried and then the crystal form A is obtained; the crystal form A is put under light in air and the stability of the crystal form A is obviously better than that of a raw material medicine.

Description

[0001] technical field [0002] The invention relates to the field of medicinal chemistry, in particular to a crystal form preparation process and application of isotretinoin. Background technique [0003] Isotretinoin (molecular formula shown in I), which belongs to retinoic acid drugs, is suitable for severe refractory nodular acne (nodular acne, that is, inflammatory lesions with a diameter ≥ 5mm, and nodules may purulent or hemorrhage ). It can also be used for pityriasis redness, acne, pityriasis redness, dermatology and other diseases. [0004] [0005] At present, documents such as US4556518, US6177579, etc. have reported the preparation method of isotretinoin, wherein the document US4556518 is reported to use β-ionone as a raw material, and obtain the raw material of isotretinoin through 4-step reaction, and the reaction formula is as follows: [0006] [0007] In addition, the document US6177579 has reported that β-ionone is used as a raw material, and the m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/20A61K31/203A61P17/10
Inventor 邓青均
Owner CHONGQING HUAPONT PHARMA
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