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Crystalline forms of 4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5- (trifluoromethyl)phenyl]-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]- benzamide salts

IP.com Disclosure Number: IPCOM000199113D
Publication Date: 2010-Aug-26
Document File: 10 page(s) / 91K

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The IP.com Prior Art Database

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Crystalline forms of 4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5- (trifluoromethyl)phenyl]-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]- benzamide salts

   4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-[[4-(3- pyridinyl)-2-pyrimidinyl]amino]-benzamide (referred to as "NLT") of the following formula:

N

C

H

3

N

F3C

NH

NH

N

O

N

N

H

3

C

is a tyrosine kinase inhibitor, used in the treatment of drug-resistant chronic myelogenous leukemia (CML).

Crystalline forms NLT acetate and succinate salts were found and are described below.

Crystalline NLT acetate form I

The crystalline form can be characterized by a powder XRD pattern having peaks at 5.4,
7.6, 8.8 degrees two theta ± 0.2 degrees two theta and broad peaks having maxima at 18.4 and 24.5 degrees two theta ± 0.2 degrees two theta degrees two theta ± 0.2 degrees two theta, a powder XRD pattern substantially as depicted in Figure 1, or a combination thereof.

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Fig. 1 shows a PXRD pattern of crystalline NLT acetate form I

5000

4000

3000

CPS

2000

1000

0

2.0 6.0 10.0 14.0 18.0 22.0 26.0 30.0 34.0 38.0

2-Tetha Scale

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Crystalline NLT acetate form II

The crystalline form can be characterized by a powder XRD pattern having peaks at 7.2,
7.8, 8.6, 10.9, 13.6, 14.4, 17.6, 18.9, 20.1 and 22.9 degrees two theta ± 0.2 degrees two theta, a powder XRD pattern substantially as depicted in Figure 2, or a combination thereof.

Fig. 2 shows a PXRD pattern of crystalline NLT acetate form II:

5000

4000

3000

2000

1000

0

CPS

2.0 6.0 10.0 14.0 18.0 22.0 26.0 30.0 34.0 38.0

2-Tetha Scale

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Crystalline NLT acetate form III

The crystalline form can be characterized by a powder XRD pattern having peaks at 3.6,
6.7, 7.7, 10.0, 15.8, 19.1, 20.3, 20.9 and 24.7 degrees two theta ± 0.2 degrees two theta, a powder XRD pattern substantially as depicted in Figure 3, or a combination thereof.

Fig. 3 shows a PXRD pattern of crystalline NLT acetate form III:

2-Tetha Scale

4000

3000

CPS

2000

1000

0

2.0 6.0 10.0 14.0 18.0 22.0 26.0 30.0 34.0 38.0

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Crystalline NLT acetate form IV

The crystalline form can be characterized by a powder XRD pattern having peaks at 4.7,
7.1, 9.5, 14.9, 19.8, 20.5 and 21.9 degrees two theta ± 0.2 degrees two theta, a powder XRD pattern substantially as depicted in Figure 4, or a combination thereof.

Fig. 4 shows a PXRD pattern of crystalline NLT acetate form IV:

2-Tetha Scale

3000

2000

CPS

1000

0

2.0 6.0 10.0 14.0 18.0 22.0 26.0 30.0 34.0 38.0

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Crystalline NLT succinate form I

The crystalline form can be characterized by a powder XRD pattern having peaks at 4.4,
5.2, 7.6, 8.8, 10.5, 11.3, 12.3, 17.3, 18.7, and 26.1 degrees two theta ± 0.2 degrees two theta, a powder XRD pattern substantially as depicted in Figure 5, or a combination thereof.

Fig. 5 shows a PXRD pattern of crystalline NLT succinate form I:

5000

4000

3000

2000

1000

CPS

02.0 6.0 10.0 14.0 18.0 22.0 26.0 30.0 34.0 38.0

2-Tetha Scale

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Crystalli...