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Crystalline forms of Calcium (2R,3S)-1-(4-amino-N-isobutylphenylsulfonamido)-4-phenyl-3-(((S)-tetrahydrofuran-3-yloxy)carbonylamino)butan-2-yl phosphate

IP.com Disclosure Number: IPCOM000196935D
Publication Date: 2010-Jun-21
Document File: 5 page(s) / 143K

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The IP.com Prior Art Database

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    Crystalline forms of Calcium (2R,3S)-1-(4-amino-N-isobutylphenylsulfonamido)-4- phenyl-3-(((S)-tetrahydrofuran-3-yloxy)carbonylamino)butan-2-yl phosphate

    Calcium (2R,3S)-1-(4-amino-N-isobutylphenylsulfonamido)-4-phenyl-3-(((S)- tetrahydrofuran-3-yloxy)carbonylamino)butan-2-yl phosphate("referred as "FSM") of the following formula;

     is a phosphate ester prodrug of the protease inhibitor and antiretroviral drug (3S)-oxolan-3- yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-1-phenylbutan-2- yl]carbamate("AMP").

Crystalline forms of FSM were found and are described herein below.

    A crystalline form of FSM, designated form II, can be characterized by data selected from: a powder XRD pattern with peaks at about 14.6, 16.5, 17.6, 19.2 and 25.4° 2θ ± 0.2° 2θ; a powder XRD pattern as depicted in figure 1, and combinations thereof. The FSM Form II can be further characterized by PXRD peaks at about 5.5, 9.5, 13.7 19.9 and 26.1° 2θ ± 0.2° 2θ.

    Figure 1 shows a powder XRD pattern of form II of FSM (peak at 28.49 degrees 2-theta belongs to Silica powder)

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    A crystalline form of FSM, designated form III, can be characterized by data selected from: a powder XRD pattern with peaks at about 20.5, 22.0, 22.7 and 29.7° 2θ ± 0.2 ° 2θ; a powder XRD pattern as depicted in figure 2, and a combination thereof. The FSM Form III can be further characterized by PXRD peaks at about 5.7, 9.8, 15.0 and 21.7° 2θ ± 0.2° 2θ.

Figure 2 shows a powder XRD pattern of form III of FSM (peak at 28.49 degrees 2-theta belongs to Silica powder)

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    A crystalline form of FSM, designated form IV, can be characterized by data selected from: a powder XRD pattern with peaks at about 20.6, 22.0, 22.8 and 26.2° 2θ ± 0.2 ° 2θ; a powder XRD pattern as depicted in figure 3, and a combination thereof. This form is an acetone solvent. The acetone solvate of FSM crystalline form IV of can be further characterized by PXRD peaks at about 5.7, 9.8, 17.9 and 26.8° 2θ ± 0.2° 2θ.

Figure 3 shows XRPD pattern of crystalline Form IV of acetone solvate of FSM

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    A crystalline form of FSM, designated form P, can be characterized by data selected from: a powder XRD pattern with peaks at about 20.6, 22.0, 22.9, 24.9 and 26.3° 2θ ± 0.2° 2θ; a powder XRD pattern as depicted in figure 4, and a combination thereof. The FSM crystalline Form P can be further characterized by PXRD peaks at about 5.7, 9.9, 28.0 and 29.6° 2θ ± 0.2° 2θ.

Figure 4 shows XRPD pattern of crystalline Form P of FSM

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PXRD method

    Samples after being powdered in a mortar and pestle are applie...