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Crystalline form of 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride and crystalline forms of S-enantiomer and of racemic 5-Chloro-N-({2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophene-carboxamide

IP.com Disclosure Number: IPCOM000198340D
Publication Date: 2010-Aug-05
Document File: 7 page(s) / 116K

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The IP.com Prior Art Database

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    Crystalline form of 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3- yl]phenyl}morpholin-3-one hydrochloride and crystalline forms of S-enantiomer and of racemic 5-Chloro-N-({2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3- oxazolidin-5-yl}methyl)-2-thiophene-carboxamide

4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one

(referred as "RVX"), of the following formula

O N

O

O

O

N

NH2

is an intermediate in the synthesis of 5-Chloro-N-({(5S)-2-oxo-3-[4-(3-oxo-4- morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophene-carboxamide("referred as "RVXN).

O

O

N O

O

N

H

N

O

S

Cl

Crystalline form of racemic RVX HCl was found and is described herein below.

The crystalline form of racemic RVX HCl salt is characterized by data selected from a powder XRD pattern with peaks at about 11.4, 18.5, 18.9, 20.6, 20.8, 22.9, 26.4, 27.4,
30.8 and 34.6 ± 0.2 degrees two-theta; a PXRD pattern depicted in Figure 1; and combination thereof.

Figure 1:a PXRD pattern of racemic RVX HCl salt crystalline form.

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Intensity (cps)

200

150

100

50

0

5 10 15 20 25 30 35

2Theta (°)

Crystalline form of racemic RVXN was found and is described herein below.

The crystalline form of racemic RVXN is characterized by data selected from a powder XRD pattern with peaks at about 12.9, 18.4, 20.5, 21.3, 23.9, 25.9, 26.4, 31.1,
34.8 and 39.3 ± 0.2 degrees two-theta; a PXRD pattern depicted in Figure 2; and combination thereof.

Figure 2:a PXRD pattern of racemic RVXN crystalline form

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Intensity (cps)

150

100

50

0

5 10 15 20 25 30 35

2Theta (°)

Two crystalline forms of RVXN were found and are described herein below. Crystalline form of RVXN is characterized by data selected from a powder XRD pattern with peaks at about 3.5, 10.6, 13.8, 14.9, 17.8, 19.5, 19.8, 20.2, 24.1 and 28.6 ± 0.2 degrees two-theta; a PXRD pattern depicted in Figure 3; and combination thereof.

Figure 3:a PXRD pattern of RVXN crystalline form prepared according to Example
3.

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Intensity (cps)

140

120

100

80

60

40

20

0

5 10 15 20 25 30 35

2Theta (°)

Crystalline form of RVXN is characterized by data selected from a powder XRD pattern with peaks at about 4.1, 12.3, 15.4, 15.7, 19.1, 19.6, 23.2, 23.7 and 28.8 ± 0.2 degrees two-theta; a PXRD pattern depicted in Figure 4; and combination thereof.

Figure 4:a PXRD pattern of RVXN crystalline form prepared according to Example
4.

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Intensity (cps)

100

80

60

40

20

0

5 10 15 20 25 30 35

Examples:

PXRD

XRD diffraction was performed on X-Ray powder diffractometer: PanAlytical X'pert Pro, CuKα radiation, λ = 1.5418 Å. X'Celerator detector active length (2 theta) =
2.122°, laboratory temperature 22-25 °C. Zero background sample holders. Prior to analysis the samples were gently ground by means of mortar and pestle in order to obtain a fine powder. The ground sample was adjusted into a cavity of the sample holder and the surface of the sample was smoothed by means of a cover glass.

Measurement para...