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Complexes of prostaglandin derivatives and monosubstituted, charged beta-cyclodextrins

A technology of prostaglandins and derivatives, applied in the field of treatment of ocular hypertension and glaucoma, can solve problems such as itching, patient discomfort, burning, etc.

Inactive Publication Date: 2010-06-30
眼科药物股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, currently marketed formulations include solubilizing compounds, such as macrogol 40 hydrogenated castor oil in the case of Suvitam or benzalkonium chloride in the case of Xalatan, which are known to cause discomfort in some patients, Even if the eyes are stinging, burning and itchy
Therefore, at least in the case of aqueous formulations, it is difficult to achieve drug effective doses because of the limited solubility of the drug without resorting to solubilizers that increase irritation

Method used

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  • Complexes of prostaglandin derivatives and monosubstituted, charged beta-cyclodextrins
  • Complexes of prostaglandin derivatives and monosubstituted, charged beta-cyclodextrins
  • Complexes of prostaglandin derivatives and monosubstituted, charged beta-cyclodextrins

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: Dissolution of Latanoprost

[0057] Libraries of unsubstituted and monosubstituted cyclodextrins were screened to identify those cyclodextrin derivatives with the highest ability to solubilize latanoprost. Complexation with cyclodextrin derivatives to latanoprost at a molar ratio of 5:1 in ultrapure water corresponds to a concentration of 115.58 mM and 23.12 mM for cyclodextrin derivatives and latanoprost, respectively. concentration. Because of the known sensitivity of latanoprost to light, high temperature, and oxidation, experiments were performed at room temperature in the dark and under nitrogen. The selectivity results are shown in Table 1. It has been found that with a single C in the glucose unit 6 Contains -NH in position 2 + -(CH 2 ) p -NH 3 + or -NH 2 + -(CH 2 ) p β-cyclodextrins with -OH (p is 2 to 6) type substituents lead to a significant increase in the water solubility of latanoprost, illustrative examples are mono-6-deoxy-6-diami...

Embodiment 2

[0061] Example 2: Latanoprost, bimatoprost and travoprost in 50 mM mono-6-deoxy-6-diaminopropyl-β-cyclodextrin, mono-6-deoxy-6-aminopropanol - Beta-cyclodextrin or solubility in water

[0062] Table 2: Dissolution of Prostaglandin Derivatives

[0063]

Embodiment 3

[0064] Example 3: Characterization of Complexation: Latanoprost-Cyclodextrin Complex

[0065] The minimum time required for the guest molecule, latanoprost, to reach maximum solubility in a solution containing 115 mM mono-6-deoxy-6-diaminopropyl-β-cyclodextrin was determined. After the addition of latanoprost, the resulting suspension was sonicated for 5 min and then stirred magnetically for 48 h at room temperature in the dark. Aliquots were removed at 0, 1, 3, 6, 12, 24 and 48 h. Each aliquot was filtered through a 0.45 μm PVDF (Millipore / Whatman) membrane, and the filtrate was diluted for quantitative analysis of latanoprost by HPLC. The results showed that the dissolution equilibrium was reached at about 24h. Subsequent experiments were performed after 24 h of equilibration.

[0066] Phase solubility diagrams were constructed to examine the increase in the solubility of latanoprost in the presence of increasing concentrations of mono-6-deoxy-6-diaminopropyl-β-cyclodextr...

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Abstract

The present invention relates to water-soluble, non-covalent complexes of a group of prostaglandin derivatives including latanoprost and monosubstituted, charged ss- cyclodextrins, as well as uses of these complexes in therapeutic compositions that are administered topically for treating intraocular hypertension and glaucoma.

Description

technical field [0001] The present invention relates to novel complexes of prostaglandin derivatives and monosubstituted β-cyclodextrins and their use in therapeutic compositions and in the treatment of ocular hypertension and glaucoma. Background technique [0002] Glaucoma is caused by an increase in relative intraocular pressure that leads to optic nerve damage and loss of visual field, Lee and Higginbotham (2005) Am. J. Health-Syst. Pharm. 62, 691-699. If left untreated, the disease can lead to irreversible blindness. Glaucoma is a common disease. In the United States alone, more than 2 million people are reported to have glaucoma, and more than 80,000 residents are legally blind as a result of the disease. The prevalence of glaucoma is especially on the rise among the elderly, African-Americans and those with diabetes, high blood pressure and nearsightedness. Glaucoma comprises a group of different diseases, of which primary open-angle glaucoma is the most common typ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
CPCC07C405/00A61K9/0048C08B37/0015B82Y5/00A61K47/48969A61K47/6951A61P27/02A61P27/06A61K47/50A61K31/557C08B37/0012
Inventor 埃尔穆斯塔法·贝尔格西尔伊夫·塞娜廷波兰德尔·加茨弗雷德里克·图尔平
Owner 眼科药物股份有限公司
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