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CRYSTALLINE FORMS OF INTERMEDIATES IN THE SYNTHESIS OF (S)-4-METHYL-N-((S)-1-(((S)-4-METHYL-1-((R)-2-METHYLOXIRAN-2-YL)- 1-OXOPENTAN-2-YL)AMINO)-1-OXO-3-PHENYLPROPAN-2-YL)-2-((S)-2-(2-MORPHOLINOACETAMIDO)-4- PHENYLBUTANAMIDO)PENTANAMIDE

IP.com Disclosure Number: IPCOM000234933D
Publication Date: 2014-Feb-17
Document File: 3 page(s) / 120K

Publishing Venue

The IP.com Prior Art Database

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CRYSTALLINE FORMS OF INTERMEDIATES IN THE SYNTHESIS OF (S)-4- METHYL-N-((S)-1-(((S)-4-METHYL-1-((R)-2-METHYLOXIRAN-2-YL)- 1-OXOPENTAN-2-YL)AMINO)-1-OXO-3-PHENYLPROPAN-2-YL)-2-((S)-2-(2-

   MORPHOLINOACETAMIDO)-4- PHENYLBUTANAMIDO)PENTANAMIDE

    For the purpose of clarity and as an aid in the understanding of the intermediates involved in the synthesis of (S)-4-Methyl-N-((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2- yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-(2-morpholinoacetamido)- 4- phenylbutanamido)pentanamide as disclosed herein, the following terms and abbreviations are defined below:

Compound MALPB (αS)-α-[[2-(4-Morpholinyl)acetyl]amino]benzenebutanoyl-L-leucyl-L-
phenylalanine phenylmethyl ester

O HN NH

Compound MALPA (αS)-α-[[2-(4-Morpholinyl)acetyl]amino]benzenebutanoyl-L-leucyl-L- phenylalanine

O HN NH

    Provided herein after, is a process for the preparation of crystalline forms of Compound MALPB and of Compound MALPA.

Crystalline Form of Compound MALPB

    The crystalline form of Compound MALPB can be characterized by an X-ray powder diffraction pattern having peaks at 7.3, 9.1, 11.5, 12.5, 13.2, 16.4, 16.9, 18.2, 18.6, 19.3, 21.0 and 22.0 degrees two theta ± 0.2 degrees two theta; and/or an X-ray powder diffraction pattern as depicted in Figure 1.

O HN OBn

N

O O

O

,

O HN OH

N

O O

O


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Intensity (counts)

6400

3600

1600

400

0

5

10

15

20

25

30

35

2Theta (°)

Figure 1. PXRD pattern of crystalline Form of Compound MALPB.

Crystalline Form of Compound MALPA

    The crystalline form of Compound MALPA can be characterized by an X-ray powder diffraction pattern having peaks at 6.6, 7.2, 8.9, 16.3, 16.9, 17.9, 19.3, 19.9, 20.3, 22.1, 24.9 and 26.5 degrees two theta ± 0.2 degrees two theta; and/or an X-ray powder diffraction pattern as depicted in Figure 2.

Intensity (counts)

19600

14400

10000

6400

3600

1600

400

0

5

10...