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Apremilast and nicotinamide co-crystal as well as preparation method and application thereof

A technology of nicotinamide and co-crystallization, which is applied to the co-crystallization of apremilast and nicotinamide and the field of preparation thereof, can solve the problems of low bioavailability and no co-crystallization of apremilast, and achieves good reproducibility , The crystallization process is easy to control and the operation is simple.

Inactive Publication Date: 2018-02-23
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Low in vivo bioavailability of apremilast due to poor solubility in water
So far, no co-crystallization of apremilast has been reported

Method used

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  • Apremilast and nicotinamide co-crystal as well as preparation method and application thereof
  • Apremilast and nicotinamide co-crystal as well as preparation method and application thereof
  • Apremilast and nicotinamide co-crystal as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] At room temperature, Apremilast (0.02mmol) and nicotinamide (0.01mmol) were added into methanol (2mL) according to the stoichiometric ratio of 2:1, and after being completely dissolved by ultrasonic oscillation, they were slowly evaporated at room temperature to obtain Apremilast and Niacinamide (0.01mmol). Co-crystallization of niacinamide. The prepared co-crystal was characterized by X-ray single crystal diffraction. The X-ray single crystal diffraction structure diagram of the co-crystal of apremilast and nicotinamide is shown in Figure 10 , The results of X-ray single crystal diffraction showed that the molar ratio of apremilast and nicotinamide was 2:1. The co-crystal of apremilast and nicotinamide is a tetragonal crystal system with a space group of P4 1 2 1 2. The unit cell parameters are: α=90°, β=90°, γ=90°, the unit cell volume is

[0068] X-ray powder diffraction (XRPD), thermogravimetric analysis (TG), differential scanning calorimetry (DSC), Raman...

Embodiment 2

[0071] At room temperature, Apremilast (0.1mmol) and nicotinamide (0.05mmol) were added into ethyl acetate (2mL) according to the stoichiometric ratio of 2:1, and after being completely dissolved by ultrasonic oscillation, slowly volatilized at room temperature to obtain Apremilast Special co-crystallization with niacinamide.

Embodiment 3

[0073] At room temperature, add apremilast (0.1mmol) and nicotinamide (0.05mmol) into a mixed solvent of methanol and ethyl acetate (1:1, each 1mL) at a stoichiometric ratio of 2:1, and dissolve completely by ultrasonic oscillation Afterwards, slowly volatilize at room temperature to obtain co-crystals of apremilast and nicotinamide.

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Abstract

The invention relates to an apremilast and nicotinamide co-crystal and a preparation method thereof. The co-crystal is subjected to comprehensive characterization by applying means including X-ray powder diffraction analysis, thermogravimetric analysis, differential scanning amount thermal analysis and the like, and the comprehensive characterization finds out that compared with apremilast, the co-crystal has better physical and chemical and drug formation performance. The preparation method of the apremilast and nicotinamide co-crystal is simple, easy to control and good in repeatability; theapremilast and nicotinamide co-crystal can be stably obtained.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and crystallization technology, and specifically relates to the co-crystallization of apremilast and nicotinamide and its preparation method and application. Background technique [0002] Drug co-crystallization (co-crystal) refers to the interaction between active pharmaceutical ingredient (API) molecules and other physiologically acceptable acids, bases, salts, non-ionic compound molecules through hydrogen bonding, π-π stacking, van der Waals forces and other non-covalent interactions. bonded together in the same crystal lattice. The greatest application value of co-crystals in drugs is that they can introduce new components without changing the covalent structure of drugs, greatly improving the physical and chemical properties of drugs, such as stability, melting point, solubility, dissolution rate, bioavailability, etc., and Since there are many types of ligands (CCF), the propert...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48C07D213/82A61K31/455A61K31/4035A61K41/00A61P17/06A61P29/00
CPCA61K31/4035A61K31/455A61K41/0057C07B2200/13C07D209/48C07D213/82A61K2300/00
Inventor 梅雪锋王逢源张奇王建荣
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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