IP Library Granted Patent US 10,759,758
Granted Patent B2
US 10,759,758 · App. 16/097,067 · Granted Sep 1, 2020

Polymorphic form of N-{6-(hydroxypropan-2-yl)-2-[2-(methylsulphonyl)ethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide

Inventors: Tobias Thaler (Köln, DE); Johannes Platzek (Berlin, DE); Nicolas Guimond (Wuppertal, DE)
Assignee: Bayer Pharma Aktiengesellschaft
C07D213/81C07D213/54C07D231/56C07D401/12C07B2200/13
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Quick Facts
Patent No.
US 10,759,758
App. No.
16/097,067
Granted
Sep 1, 2020
Kind
B2
Abstract

The present invention relates to crystalline forms of N-{6-(2-Hydroxypropan-2-yl)-2-[2-(methylsulphonyl)ethyl]-2H-indazol-5-yl}-6-(trifluoromethyl)pyridine-2-carboxamide, to processes for their preparation, to pharmaceutical compositions comprising them and to their use in the control of disorders.

Claims (21)

1. A crystalline form of the compound of the formula (I)

selected from the group consisting of polymorph A, polymorph B and 1,7-hydrate, or a mixture thereof,

wherein the polymorph A has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.20: 9.2, 9.8 and 19.3;

wherein the polymorph B has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.20: 9.7, 10.1, and 15.4; and

wherein the 1,7-hydrate has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.20: 10.6, 11.8, and 14.5.

2. The crystalline form of the compound of claim 1 , which is polymorph B.

3. The form of the compound of claim 1 , which is polymorph B has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.20: 9.7, 10.1, 15.4, 16.1, and 20.2.

4. The form of the compound of claim 1 , which is polymorph B has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.20: 9.7, 10.1, 15.4, 16.1, 20.2, and 22.3.

5. The form of the compound of claim 1 , which is polymorph B has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.20: 9.7, 10.1, 15.4, 16.1, 20.2, 22.3, and 25.2.

6. A pharmaceutical composition comprising only one of the crystalline forms selected from the group consisting of polymorphic form A, polymorphic form B, and 1,7-hydrate of the compound of formula (I) according to claim 1 ,

wherein the polymorph A has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.2°: 9.2, 9.8 and 19.3;

wherein the polymorph B has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.2°: 9.7, 10.1, and 15.4; and

wherein the 1,7-hydrate has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.2°: 10.6, 11.8, and 14.5.

7. A pharmaceutical composition comprising a crystalline form of the compound of formula (I)

selected from the group consisting of polymorphic form A, polymorphic form B, and 1,7-hydrate, an amorphous form or a mixture thereof and pharmaceutically acceptable excipients,

wherein the polymorph A has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.2°: 9.2, 9.8 and 19.3;

wherein the polymorph B has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.2 °: 9.7, 10.1, and 15.4; and

wherein the 1,7-hydrate has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value±0.20: 10.6, 11.8, and 14.5.

8. The pharmaceutical composition of claim 7 , comprising only polymorphic form B of the compound of formula (I).

9. The pharmaceutical composition of claim 7 , comprising polymorphic form B of the compound of formula (I) in more than 85 percent by weight related to the total amount of all forms of the compound of formula (I) present in the composition.

10. The pharmaceutical composition of claim 9 , comprising polymorphic form B of the compound of formula (I) in more than 90 percent by weight related to the total amount of all forms of the compound of formula (I) present in the composition.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 29, 2019
From: THALER, TOBIAS; PLATZEK, JOHANNES; GUIMOND, NICOLAS
To: BAYER PHARMA AKTIENGESELLSCHAFT
Reel/Frame 049891/0288 →
Priority Claims (1)
EP 16167652 · Apr 29, 2016 · regional
Continuity (1)
Related Publication 20190112270A1 · Apr 18, 2019
Cited By (2)
US 12,241,109 US 12,559,473