CRYSTALLINE FORMS OF C21H22Cl2N4O2
AssigneesBiomed Valley Discoveries, Inc., Vertex Pharmaceuticals Incorporated
InventorsGary DeCrescenzo, Dean Welsch, Petinka I. Vlahova, Stephan X.M. Boerrigter, Alexander Aronov, Ali Keshavarz-Shokri, Alexander N. Scangas, Kathy Stavropoulos, Benjamin Littler, Irina Nikolaevna Kadiyala, Rossitza Gueorguieva Alargova
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Abstract
The present invention provides crystalline forms of a compound of formula (I): Also provided are pharmaceutical compositions that include the provided crystalline forms and methods of using the provided crystalline forms and pharmaceutical compositions for the treatment of cancer.
Claims38
A method of preparing a crystalline form of a compound of formula (I):
- comprising the steps of:
- (a) providing a mixture comprising the compound of formula (I) in an organic solvent;
- (b) adding anhydrous sodium sulfate to the mixture of step (a);
- (c) concentrating the mixture of step (b);
- (d) adding MTBE to the mixture of step (c);
- (e) cooling the mixture of step (d);
- and
- (f) filtering the mixture of step (e) to isolate the crystalline form of formula (I).
A crystalline free base of a compound of formula (I):
- having an X-ray powder diffraction (XRPD) pattern comprising characteristic peaks at about 12.5, 23.3 and 23.6° 2θ.
A crystalline free base 4-(5-Chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide mono HCl having a Fourier transform infrared spectroscopy (FT-IR) spectrum comprising one or more peaks at about 783, 827, 1523, and 1629 cm−1.
A crystalline hydrochloride salt of a compound of formula (I):
- having an X-ray powder diffraction (XRPD) pattern comprising characteristic peaks at about 20.8, 24.9, and 25.4° 2θ.
A form C crystalline 4-(5-Chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide mono HCl having a Fourier transform infrared spectroscopy (FT-IR) spectrum comprising one or more peaks at about 694, 771, 785, and 1643 cm−1.
A crystalline hydrochloride salt of a compound of formula (I):
- having an X-ray powder diffraction (XRPD) pattern comprising characteristic peaks at about 17.6, 24.9, and 29.8° 2θ.
A form A crystalline 4-(5-Chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide HCl hydrate having a Fourier transform infrared spectroscopy (FT-IR) spectrum comprising one or more peaks at about 844, 1215, 1309, 1599, 1613, 1631, and 1648 cm−1.
A crystalline hydrochloride salt of a compound of formula (I):
- having an X-ray powder diffraction (XRPD) pattern comprising characteristic peaks at about 6.3, 12.0, 16.3, 21.7, and 27.4° 2θ.
A form D crystalline 4-(5-Chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide HCl having a Fourier transform infrared spectroscopy (FT-IR) spectrum comprising one or more peaks at about 787, 846, 1239, 1613, 1631, and 1647 cm−1.
A form A crystalline 4-(5-Chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide HCl hydrate having a Raman spectroscopy spectrum comprising one or more peaks at about 983 and 1165 cm−1.
A form C crystalline 4-(5-Chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide mono HCl having a Raman spectroscopy spectrum comprising a peak at about 987 cm−1.
Crystalline 4-(5-Chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide.
Crystalline free base 4-(5-Chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide.
Crystalline 4-(5-Chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide mono HCl.
Crystalline 4-(5-Chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide HCl hydrate.
Dependencies are inferred from the claim text.