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POLYMORPHS OF N-[3-CHLORO-4-[(3-FLUOROPHENYL)METHOXY]PHENYL]-6- [5-[(2-METHYLSULFONYLETHYLAMINO)METHYL]-2-FURYL]QUINAZOLIN-4-AMINE MONOTOSYLATE

IP.com Disclosure Number: IPCOM000199806D
Publication Date: 2010-Sep-16
Document File: 3 page(s) / 23K

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The IP.com Prior Art Database

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POLYMORPHS OF N-[3-CHLORO-4-[(3-FLUOROPHENYL)METHOXY]PHENYL]-6-

[5-[(2-METHYLSULFONYLETHYLAMINO)METHYL]-2-FURYL]QUINAZOLIN-4-

AMINE MONOTOSYLATE

N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-ethylsulfonylethylamino)methyl]- 2-furyl]quinazolin-4-amine ditosylate, has the following chemical structure:

O

S

F

O

O

Cl

N

H

N

H

N

N

x 2HO3S CH3

O

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Scanning parameters: range: 2-40 degrees two-theta; scan mode: continuous scan; step size:
0.05°.; and a rate of 3 deg/min.

Form XXI:
To 0.5 gr solid N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6- [5-[(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine ditosylate sample 50V Cellosolve (ethoxyethanol) was added and yellow suspension was obtained. The resulted suspension was heated to reflux (135C), to obtain yellow solution. Resulted solution was cooled over 1h to 25°C to obtain yellow suspension, whereupon it was filtered. The cake thus obtained was identified as Form XXI.

The product was analyzed by X-ray powder diffraction and its XRD peaks are represented by the characteristic XRPD pattern: Main XRD peaks of Form XXI prepared according to the method above are: 4.2, 8.5, 12.7, 14.2, 15.2, 15.5, 18.9, 19.4, 20.0, 21.0, 21.4, 22.7, 23.2,
24.4 and 25.8 ± 0.2 degrees 2-theta.

The analysis was performed on ARL (SCINTAG) powder X-Ray diffractometer model X'TRA equipped with a solid state detector. Copper radiation of 1.5418 Å was used. Scanning parameters: range: 2-40 degrees two-theta; scan mode: continuous scan; step size:
0.05°.; and a rate of 3 deg/min.

Form XXII:
Mixture of 1.00 g (1.72 mmol) N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6- [5-[(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine, 0.66 g (3.47 mmol) p- TSA•H2O and 30 ml (30V) o...