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2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl}methyl)benzonitrile Co-Crystal of Benzoate and Phenol

IP.com Disclosure Number: IPCOM000181860D
Publication Date: 2009-Apr-16
Document File: 4 page(s) / 97K

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2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)- yl}methyl)benzonitrile Co-Crystal of Benzoate and Phenol

    2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin- 1(2H)-yl}methyl)benzonitrile ("ALG") of the following formula

    is a selective dipeptidyl peptidase-4 (DPP-4) inhibitor. This enzyme-inhibiting drug is used either alone or in combination with metformin or pioglitazone for the control of type 2 diabetes.

A co-crystal of ALG benzoate and phenol was found and is described herein.

    The co-crystal of ALG benzoate and phenol is characterized by data selected from a group consisting of a powder XRD pattern with XRD peaks at 7.7, 8.4, 10.7, 12.3,
16.3, 18.0, 18.5, 19.1, 19.6, 20.6, 21.6, 23.5, 25.3 ± 0.2 degrees theta and a PXRD pattern as shown in Figure 1.

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Figure 1. PXRD pattern of ALG benzoate:phenol cocrystal.

Intensity(counts)

6400

3600

1600

400

0

5 10 15 20 25 30 35

2Theta (°)

    The co-crystal of ALG benzoate and phenol can be further characterized by a DSC pattern as shown in Figure 2.

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Figure 2. DSC thermogram of ALG benzoate:phenol cocrystal.

PXRD method:

After powdering the samples with a mortar and pestle, they were applied directly to a silicon plate holder. The X-ray powder diffraction pattern was measured with Philips X'Pert PRO X-ray powder diffractometer, equipped with Cu irradiation source =1.54184 Ǻ (Ǻngström), X'Celerator (2.022º 2-theta) detector. Scanning parameters: angle range: 3-40...