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Nutraceutical co-crystal compositions

a technology of co-crystals and compositions, which is applied in the field of co-crystal compositions containing, can solve the problems of relatively unexplored co-crystals and the acquisition of non-uniform mixtures, and achieve the effects of improving animal health or nutrition, improving properties, and increasing aqueous solubility and stability

Inactive Publication Date: 2010-08-12
UNIV OF SOUTH FLORIDA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0012]Among the various aspects of the invention is the provision of nutraceutical co-crystals, a process for the preparation of such co-crystals, and methods for improving animal health or nutrition by administering such co-crystals (alone or in combination with other compositions or as a component thereof) to a human or other animal. Advantageously, the nutraceutical co-crystals provide improved properties, in particular, as oral formulations. Such properties may include one or more of increased aqueous solubility and stability, improved processability, improved biological activity, improved biological availability, improved dissolution, and improved plasma profile. In addition, the properties may be altered in a way which is most beneficial to a specific nutraceutical for a specific therapeutic effect. These crystalline forms possess a range of desirable properties and may be used as a nutraceutical, as part of a pharmaceutical composition, nutritional supplements, foodstuffs, and the like.

Problems solved by technology

AD is a devastating neurodegenerative disease that currently affects an estimated 4.5 million Americans, costing the United States more than $100 billion annually.
However, co-crystals remain relatively unexplored.
For example, needle-like crystal forms or habits of nutraceuticals can cause aggregation, even in compositions where the nutraceutical is mixed with other substances, such that a non-uniform mixture is obtained.

Method used

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  • Nutraceutical co-crystal compositions
  • Nutraceutical co-crystal compositions
  • Nutraceutical co-crystal compositions

Examples

Experimental program
Comparison scheme
Effect test

example 1

Methanol Solvate of Co-Crystal of Quercetin and Caffeine—KP05

[0174]34.0 mg (0.101 mmol) of quercetin dehydrate (98% pure, Sigma Aldrich) and 19 mg (0.100 mmol) of caffeine (Sigma Aldrich) were dissolved in approximately 6 mL methanol by heating. Slow evaporation of the solvent yielded golden yellow crystals of quercetin:caffeine (1:1) co-crystal (hereinafter, “KP05”). A digital microscopic image of KP05 is shown in FIG. 1 of the accompanying drawings. The reaction scheme is shown below:

[0175]KP05 was characterized by DSC analysis, which showed phase changes at about 144° C. and about 246° C. The DSC graph is shown in FIG. 2 of the accompanying drawings.

[0176]KP05 can be characterized using XRPD, and exhibited major peaks at about the following positions: 8.6, 10.5, 18.2, 24.2, 26.3, 29.2, and 31.2 degrees. The experimental XRPD graph for KP05 is shown in FIG. 3 of the accompanying drawings. The calculated XRPD graph for KP05 is shown in FIG. 4 of the accompanying drawings, and a com...

example 2

Co-Crystal of Quercetin and Iso-Nicotinamide—KP10

[0181]34.0 mg (0.101 mmole) of quercetin dehydrate (98% pure, Sigma Adrich) and 12.3 mg (0.100 mmol) iso-nicotinamide (Sigma Aldrich) were dissolved in approximately 6 mL of methanol by heating. The resulting solution was cooled in a refrigerator and allowed to stand for two days. Slow evaporation yielded golden yellow crystals of 1:1 quercetin:iso-nicotinamide co-crystal (hereinafter “KP10”). A digital microscopic image of KP10 is shown in FIG. 10 of the accompanying drawings. KP10 can also be prepared by slurrying in methanol overnight. The reaction scheme is shown below:

[0182]DSC analysis was performed on KP10 and showed a phase change at about 262° C. The DSC graph is shown in FIG. 11 of the accompanying drawings.

[0183]KP10 can be characterized using XRPD, and exhibited major peaks at about the following positions: 6.2, 7.7, 14.1, 15.4, 21.5, 24.0, 26.5, 27.9, and 30.9 degrees. The experimental XRPD graph for KP10 is shown in FIG....

example 3

Co-Crystal of Hesperetin and Iso-Nicotinamide—KP15

[0188]30.2 mg (0.0100 mmol) hesperetin (95% pure, Sigma Aldrich) and 12.2 Mg (0.0100 mmol) iso-nicotinamide (99% pure, Sigma Aldrich) were dissolved in approximately 8 mL of methanol by heating. The resulting solution was cooled in a refrigerator and allowed to stand for one week. This slow evaporation yielded colorless crystals of 1:1 hesperetin:iso-nicotinamide co-crystal (hereinafter “KP15”). DSC analysis showed a phase change at about 180° C.

[0189]KP15 can be characterized using XRPD, and exhibited major peaks at about the following positions: 3.6, 7.1, 10.6, 12.6, 14.2, 17.8, 19.1, 20.7, 25.0, 26.5, and 29.0 degrees. The XRPD graph for KP15 is shown in FIG. 19 of the accompanying drawings.

[0190]Hydrogen bonding occurs between two of the phenolic —OH moieties of hesperetin molecules and the following: other hesperetin molecules and the pyridyl moieties of iso-nicotinamide dimmers (OH . . . O−2.720(2) Å, OH . . . N=2.623(1) Å). Th...

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Abstract

Co-crystals comprising at least one nutraceutical compound and at least one co-crystal former with or without impurities. These co-crystals may be included in compositions (optionally also including other components such as pharmaceutically acceptable excipients, other nutritional supplements, etc.) having utility as pharmaceuticals, nutraceuticals, nutritional supplements, and foodstuffs.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Provisional Patent Application Ser. No. 60 / 942,355 filed Jun. 6, 2007, and the benefit of U.S. Provisional Patent Application Ser. No. 60 / 982,619, filed Oct. 25, 2007, the contents of each of these prior provisional patent applications being incorporated herein by reference in its entirety.FIELD OF THE INVENTION[0002]The present invention is generally related to co-crystal compositions containing nutraceuticals. Such compositions may be used in the preparation of (or even as) pharmaceuticals, nutraceuticals, nutritional supplements, food compositions and the like.BACKGROUND ART[0003]Nutraceuticals are a class of natural product that is attracting increasing attention. Nutraceuticals refer to a food or food component claimed to human health benefits. Nutraceuticals more specifically relate to individual chemicals present in foods and are commonly marketed as dietary supplements. Examples of nutra...

Claims

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Application Information

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IPC IPC(8): A61K31/55A61K31/522A61K31/44A61K31/35A61K31/34A61K31/19
CPCA23L1/30C07D401/14A61K31/55A61K31/20A23L33/10A61K31/197A61K31/375A61K31/455A61K31/522
Inventor ZAWOROTKO, MICHAELCLARKE, HEATHERKAPILDEV, ARORAKAVURU, PADMINISHYTLE, ROLAND DOUGLASPUJARI, TWARITAMARSHALL, LISSETTEONG, TIEN TENG
Owner UNIV OF SOUTH FLORIDA
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