IP Library › Granted Patent US 12,649,732
Granted Patent B2
US 12,649,732 · App. 17/627,590 · Granted Jun 9, 2026

Polymorphs of (R)-N-(5-(5-isopropyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-2-methyl-2H-tetrazole-5-carboxamide

Inventors: Norma Tom (Belmont, CA); Denise Andersen (Montara, CA)
Assignee: CYTOKINETICS, INC.
C07D413/12C07B2200/13
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Quick Facts
Patent No.
US 12,649,732
App. No.
17/627,590
Granted
Jun 9, 2026
Kind
B2
Abstract

Provided herein are polymorphs of (R)—N-(5-(5-isopropyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-2-methyl-2H-tetrazole-5-carboxamide, compositions thereof, methods of preparation thereof, and methods of their uses.

Claims (18)

1 . A polymorph of (R)—N-(5-(5-isopropyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-2-methyl-2H-tetrazole-5-carboxamide of Form I or Form II, wherein

Form I is characterized by having an XRPD pattern comprising peaks at angles 2-theta of 7.1±0.2, 14.2±0.2, 14.9±0.2, 16.2±0.2, and 18.3±0.2 degrees; and

Form II is characterized by having an XRPD pattern comprising peaks at angles 2-theta of 14.9±0.2, 16.0±0.2, 18.8±0.2, 22.5±0.2, and 25.8±0.2 degrees.

2 . The polymorph of Form I of claim 1 , characterized by having an XRPD pattern comprising peaks at angles 2-theta of 7.1±0.2, 14.2±0.2, 14.9±0.2, 16.2±0.2, and 18.3±0.2 degrees.

3 . The polymorph of Form I of claim 1 , characterized by having an XRPD pattern comprising peaks at angles 2-theta of 7.1±0.2, 9.9±0.2, 14.2±0.2, 14.9±0.2, 16.2±0.2, 17.6±0.2, 18.3±0.2, 21.0±0.2, 24.1±0.2, and 24.5±0.2 degrees.

4 . The polymorph of Form I of claim 1 , characterized by having an endotherm onset at 153±2° C. as determined by DSC.

5 . The polymorph of Form II of claim 1 , characterized as having an XRPD pattern comprising peaks at angles 2-theta of 14.9±0.2, 16.0±0.2, 18.8±0.2, 22.5±0.2, and 25.8±0.2 degrees.

6 . The polymorph of Form II of claim 1 , characterized as having an XRPD pattern comprising peaks at angles 2-theta of 5.7±0.2, 9.4±0.2, 13.6±0.2, 14.9±0.2, 16.0±0.2, 18.8±0.2, 22.5±0.2, 22.7±0.2, 23.1±0.2, and 25.8±0.2 degrees.

7 . The polymorph of Form II of claim 1 , characterized as having an endotherm onset at 133±2° C. as determined by DSC, and/or an exotherm onset at 135±2° C. as determined by DSC, and/or an endotherm onset at 152±2° C. as determined by DSC.

8 . A method of preparing a polymorph of Form I of claim 1 , comprising:

(1) forming a mixture of (R)—N-(5-(5-isopropyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-2-methyl-2H-tetrazole-5-carboxamide and a solvent, wherein the solvent comprises acetonitrile; and

(2) cooling or evaporating the mixture of step (1).

9 . The method of claim 8 , wherein step (1) comprises heating the mixture to 70±5° C.

10 . The method of claim 8 , wherein step (2) comprises cooling the mixture of step (1) to ambient temperature.

11 . The method of claim 8 , wherein an anti-solvent is added before step (2) is performed, wherein the anti-solvent is water.

12 . A method of preparing a polymorph of Form II of claim 1 , comprising:

(1) forming a mixture of polymorphic Form I of (R)—N-(5-(5-isopropyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-2-methyl-2H-tetrazole-5-carboxamide and a solvent, wherein the solvent comprises n-propyl acetate; and

(2) removing the solvent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2022
From: TOM, NORMA; ANDERSEN, DENISE
To: CYTOKINETICS, INC.
Reel/Frame 059286/0874 →
Continuity (2)
Provisional Application 62875355 · Jul 17, 2019
Related Publication 20220274969A1 · Sep 1, 2022
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