Browse Prior Art Database

Crystalline form of 2-(6-Chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylpentyl)thiazole-5-carboxamide

IP.com Disclosure Number: IPCOM000174102D
Publication Date: 2008-Aug-26
Document File: 5 page(s) / 122K

Publishing Venue

The IP.com Prior Art Database

This text was extracted from a PDF file.
At least one non-text object (such as an image or picture) has been suppressed.
This is the abbreviated version, containing approximately 58% of the total text.

Page 1 of 5

Crystalline form of 2-(6-Chloro-2-methylpyrimidin-4-ylamino)- N-(2-chloro-6-methylpentyl)thiazole-5-carboxamide

     Crystalline form of 2-(6-Chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6- methylpentyl)thiazole-5-carboxamide (referred to as Compound 5D) of the following formula:

CH3

CH3

N

N

N

H

Cl O

N

S

N

H

Cl

1

    is an intermediate in the preparation of N-(2-chloro-6-methylphenyl)-2-(6-(4-(3- hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazol-5-carboxamide having the following formula:

CH3

CH3

N

N

N

H

Cl O

N

S

N

H

N

N OH

2

    N-(2-chloro-6-methylphenyl)-2-(6-(4-(3-hydroxyethyl)piperazin-1-yl)-2- methylpyrimidin-4-ylamino)thiazol-5-carboxamide is marketed under the trade name Sprycel ® by Bristol-Myers Squibb Company.

    The preparation of N-(2-chloro-6-methylphenyl)-2-(6-(4-(3- hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazol-5-carboxamide and Compound 5D are described in US 6,596,746 B1. Another synthetic route for Compound 5D is disclosed in the patent application US2006/0004067 A1.

Page 2 of 5

    When performing the procedure according to example 5D of US2006/0004067 A1 a crystalline form of Compound 5D is obtained and it is described herein below. The form has main diffraction peaks at about 10.7, 13.4, 18.2, 18.5, 21.4, 22.5, 26.1 and 26.9 ± 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 on Figure 1 andtable 1.

    The above crystalline form can be further characterized by FTIR spectrum and a peak list described on Figure 2 andtable 2.

Figure 1

[This page contains 1 picture or other non-text object]

Page 3 of 5

Table 1

Peak Position [°2Th.]

Relative Intensity [%]

10.7 8.295 19.9
13.4 6.597 14.8
13.5 6.539 11.3
14.1 6.268 3.0
16.7 5.308 7.5
17.3 5.131 6.1
17.9 4.959 19.0
18.2 4.881 51.0
18.5 4.784 26.3
19.2 4.627 8.2
19.5 4.560 9.3
20.4 4.345 2.0
21.4 4.152 14.0
22.5 3.947 16.0
24.2 3.685 5.0
25.5 3.493 3.3
26.1 3.417 100.0
26.9 3.320 63.6
27.3 3.270 6.1
28.0 3.190 4.0
28.4 3.138 6.2
29.0 3.077 3.9
29.8 3.002 6.1
30.8 2.900 8.3
31.4 2.846 7.0
33.0 2.715 6.0
33.3 2.691 3.0
34.0 2.635 2.5
34.5 2.598 2.7
34.8 2.577 3.5
36.1 2.489 6.2
37.4 2.402 10.6

d-spacing [Ǻ]

Figure 2

Page 4 of 5

6

...