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Crystalline form of 2-Amino-N-(2-chloro-6-methylpentyl) thiazole-5-carboxamide

IP.com Disclosure Number: IPCOM000175618D
Publication Date: 2008-Oct-16
Document File: 5 page(s) / 111K

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Crystalline form of 2-Amino-N-(2-chloro-6-methylpentyl) thiazole-5-carboxamide

     The compound 2-Amino-N-(2-chloro-6-methylpentyl)thiazole-5-carboxamide ("DAS-5") of the following molecular formula:

is a starting material for the preparation of N-(2-chloro-6-methylphenyl)-2-(6-(4-(3- hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazol-5-carboxamide ("DAS") of the following formula.

    DAS is marketed under the trade name Sprycel ® by Bristol-Myers Squibb Company, for treatment of patients with chronic yelogenous leukemia (CML) after imatinib treatment and Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph+ ALL). It is also being assessed for treatment of metastatic melanoma.

    A crystalline form of DAS-5 was found and is described herein below. The form has main diffraction peaks at about 10.5, 14.5, 15.4, 16.3, 20.7, 23.7, 25.4 and 26.5 ± 0.2 deg 2-theta. In addition, the above crystalline form can be further characterized by a powder XRPD pattern and a peak list described in Figure 1 and Table 1, respectively.

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Figure 1:A powder XRD pattern of crystalline DAS-5 prepared following the procedure in example 1.

Table 1: A list of XRD peaksof crystalline DAS-5 prepared following the procedure in example 1.

Peak Position [°2Th.]
10.5
10.7
11.6
14.5
15.4
15.5
15.9
16.3
16.5
17.8
18.6
18.9
20.7
21.2
21.4

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Peak Position [°2Th.]
23.3
23.7
24.0
24.1
24.6
25.4
26.5
26.5
26.9
27.0
27.9
28.6
28.9
29.2
30.1
30.3
31.0
31.8
32.0
32.2
33.2
33.5
33.7
34.7
35.5
36.0
36.1
37.3
38.2
38.6
39.4
39.8

In addition, the above crystalline form can be further characterized by FTIR spectrum and a peak list described in Figure 2 and Table 2, respectively.

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Figure 2: IR spectrum of crystalline DAS-5 prepared following the procedure in example 1.

0,28

0,26

0,24

0,22

0,20...