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Crystalline 2-(2-amino-3-benzoylphenyl)acetamide

IP.com Disclosure Number: IPCOM000179312D
Publication Date: 2009-Feb-12
Document File: 5 page(s) / 81K

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Crystalline 2-(2-amino-3-benzoylphenyl)acetamide

2-(2-amino-3-benzoylphenyl)acetamide ("NPFC") of the following formula

O

is a non-steroidal anti-inflammatory prodrug. It is metabolized and undergoes an enzymatic hydrolysis that converts it to 2-amino-3-benzoylbenzene acetic acid monohydrate.

    NPFC is marketed as an ophthalmic suspension by Alcon Laboratories Inc. under the name NEVANAC®.

Crystalline NPFC is characterized by PXRD diffraction peaks at about 5.87, 11.73,
13.28, 17.39, 17.63, 21.98, 22.36, 23.57 and 25.04°+0.20 degrees two theta. Crystalline NPFC is further characterized by a PXRD as depicted in figure 1.

Figure 1: PXRD spectrum of crystalline NPFC.

The X-Ray powder diffraction data was obtained using a Philips X'Pert PRO powder diffractometer equipped with X'Celerator detector (active length 2Θ = 2.022°), CuKα radiation, λ = 1,540598Å at laboratory temperature 22-25°C

Example 1: Preparation of crystalline NPFC
2-(2-amino-3-benzoylphenyl)acetamide (50 mg) was added to 4 ml of ethanol and the mixture heated to facilitate dissolving of the 2-(2-amino-3-benzoylphenyl)acetamide. The resulting solution was left under ambient conditions at room temperature and allowed to crystallize as

NH2

O

NH2

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the temperature of the solution decreased. 36 mg of 2-(2-amino-3-benzoylphenyl)acetamide was obtained.

Example 2: Preparation of crystalline NPFC
2-(2-amino-3-benzoylphenyl)acetamide (50 mg) was dissolved in 4 ml of acetone by heating at about 45-50°C. The prepared solution was left at room conditions to crystallize. After 2 days at room conditions 23 mg of 2-(2-amino-3-benzoylphenyl)acetamide was obtained.

Example 3: Preparation of crystalline NPFC
2-(2-amino-3-benzoylphenyl)acetamide (50 mg) was dissolved in 5 ml of dichloromethane by heating at about 30-35°C. The prepared solution was left at room conditions to crystallize. After 2 days at room conditions 18 mg of 2-(2-amino-3-benzoylphenyl)acetamide was obtained.

Example 4: Preparation of crystalline NPFC
2-(2-amino-3-benzoylphenyl)acetamide (50 mg) was dissolved in 10 ml of diethyl ether by heating at about 30°C. The prepared solution was left at room conditions to crystallize. After 30 days at room conditions 15 mg of 2-(2-amino-3-benzoylphenyl)acetamide was obtained.

Example 5: Preparation of crystalline NPFC
2-(2-amino-3-benzoylphenyl)acetamide (50 mg) was dissolved in 4 ml of acetonitrile by heating at about 75-80°C. The prepared solution was left at room conditions to crystallize. After 2 days at room conditions 32 mg of 2-(2-amino-3-benzoylphenyl)acetamide was obtained.

Example 6: Preparation of crystalline NPFC
5 2-(2-amino-3-benzoylphenyl)acetamide (50 mg) was dissolved in 6 ml of benzonitrile by heating at about 100°C. The prepared solution was left at room conditions to cryst...