New crystals of a benzoylbenzeneacetamide derivative

A technology of crystals and drugs, applied in the field of preparation of pharmaceutical preparations, nepafenac crystals, can solve the problems of suspension filtration difficulties, easy blocking, easy bridging, etc.

Inactive Publication Date: 2012-05-02
MEDICHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Likewise, crystals of known needle-like shape are undesirable because, for example, filtration of suspensions of such needle-like crystals is known to be difficult, and loose materials containing such needle-like crystals are difficult to weigh, process and Can be prone to jamming or bridging in transport units

Method used

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  • New crystals of a benzoylbenzeneacetamide derivative
  • New crystals of a benzoylbenzeneacetamide derivative
  • New crystals of a benzoylbenzeneacetamide derivative

Examples

Experimental program
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specific Embodiment

[0072] The following examples further illustrate the invention but, of course, should not be construed as in any way limiting its scope.

[0073] General Experimental Conditions

[0074] Particle size distribution method:

[0075] The particle size of nepafenac was measured using a Malvern Mastersizer S particle size analyzer with MS1 - small volume sample dispersion unit stirred cell. A 300RF mm lens and a 2.4mm beam length were used. Samples for analysis were prepared by wetting a weighed amount of nepafenac (approximately 50 mg) with 0.5 mL of 1% Igepal CA-630 in deionized water and dispersing in 20 mL of deionized water. After 1 min of sonication, the suspension was delivered dropwise into a previously backgrounded and corrected measurement chamber filled with dispersant (deionized water) until obscuration reached the desired level. A cubic volume distribution is obtained. After the measurement is complete, the sample chamber is emptied and cleaned, refilled with suspe...

Embodiment 1

[0099] Nepafenac obtained in Examples 1-4 showed plate-shaped crystals ( FIG. 4 ). When these crystals were treated with metallic materials, a reduced charge rate was observed compared to needle-like crystals. Aspect ratio: 3.04 (Example 1).

Embodiment 5

[0106] Example 5: Preparation of 2-amino-3-benzoylphenylacetamide (i.e., nepafenac) crystals in the form of flakes

[0107] 310 g of nepafenac were dissolved in 7.5 L of a 2-propanol:water mixture 90:10 at reflux temperature with mechanical stirring. The solution was cooled to 20°C and stirred at this temperature. The solid was filtered and dried under vacuum at 60 °C until constant weight.

[0108] The obtained nepafenac showed plate-shaped crystals (Fig. 5). When these crystals were treated with metallic materials, a reduced charge rate was observed compared to needle-like crystals.

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Abstract

The invention relates to 2-amino-3-benzoylbenzeneacetamide, i.e. nepafenac, crystals having reduced chargeability, to processes for the preparation thereof, and to the use thereof for preparing pharmaceutical formulations.

Description

Background of the invention [0001] Nepafenac (Compound I) is the internationally accepted name of 2-amino-3-benzoylphenylacetamide and has the empirical formula C 15 h 14 N 2 o 2 , and a molecular weight of 254.28. [0002] [0003] Nepafenac is an active non-steroidal anti-inflammatory drug with analgesic activity. In the United States, nepafenac is known under the name Nevanac TM It is marketed as a suspension and labeled for ophthalmic use. [0004] The preparation of nepafenac and similar compounds is disclosed in US Patent No. 4,313,949. Specifically, Example 2 of US Patent No. 4,313,949 describes the synthesis of nepafenac, which was isolated as yellow needles after crystallization from isopropanol. [0005] However, it is well known that needle-shaped crystals have high electrostatic properties, which cause processability problems, ie, sticking, looseness, difficulty in filtration, etc. caused by static electricity. Also, such crystals of electrostatic nature...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/20A61K31/165A61P27/02A61P29/00
CPCC07C237/20Y10T428/2982A61P27/02A61P29/00
Inventor 安娜·加瓦尔达埃斯库多欧内斯特·杜兰洛佩兹
Owner MEDICHEM
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