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Solid state form of 4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]- 3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-benzamide fumarate

IP.com Disclosure Number: IPCOM000245814D
Publication Date: 2016-Apr-12
Document File: 2 page(s) / 68K

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Solid state form of 4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]- 3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-benzamide fumarate

    Described herein is a crystalline form of 4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5- (trifluoromethyl)phenyl]-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-benzamide fumarate, referred herein as Compound I.

    Samples of Compound I were prepared by the processes described in examples 1-3, and were analyzed by X-ray powder diffraction ("XRPD") to provide a crystalline form. Figure 1 presents the XRPD of the obtained form.

Figure 1: An X-ray powder diffraction pattern of the crystalline form of Compound I

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    According to figure 1, the crystalline form of Compound I is characterized by XRPD peaks at: 5.5, 7.0, 11.0, 13.4, 14.0, 14.9, 15.8, 16.3, 20.4, 20.5, 20.9 and 25.3 degrees 2-theta ±
0.2 degrees 2-theta.

X-ray Powder diffraction pattern ("XRPD") method:

The sample, after being powdered in a mortar and pestle, is applied directly on a silicon plate holder. The X-ray powder diffraction pattern was measured with a Philips X'Pert PRO X-ray powder diffractometer, equipped with Cu irradiation source = 1.54184 Ǻ (Angstrom), and an X'Celerator (2.022º 2θ) detector. Scanning parameters: angle range: 3-40 °, step size 0.0167, time per step 37 s, continuous scan. The described peak positions were determined using silicon powder as an internal standard in an admixture with the sample measured.

Intensity (counts)

5 10 15 20 25 30 35 2Theta (°)


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Examples

    The starting material, 4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)- phenyl]-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-benzamide base can be prepared according to the process described for example in WO2011/0163222.

Example 1: Preparation of crystalline form of Compound I

    4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-[[4-(3- pyridinyl)-2-pyrimidinyl]amino]-benzamide base (1.0 g;...