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US 8,604,215 B2Granted
Crystalline tripeptide epoxy ketone protease inhibitors
AssigneeOnyx Therapeutics, Inc.
InventorsPasit Phiasivongsa, Louis C. Sehl
Life of this patent
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Abstract
The invention relates to crystalline tripeptide keto epoxide compounds, methods of their preparation, and related pharmaceutical compositions. In addition, the compounds provided herein are immunoproteasome inhibitors and are useful, for example, in the treatment of cancer and autoimmune disease. In some cases, a compound provided herein is a compound of Formula (II):
Claims20
A method for preparing a crystalline compound of Formula (II)
- comprising (i) preparing a solution of a compound of Formula (II) in an organic solvent;
- (ii) bringing the solution to supersaturation to cause formation of crystals;
- and (iii) isolating the crystals,
- wherein the crystalline compound has 2θ values 8.94;
- 9.39;
- 9.76;
- 10.60;
- 11.09;
- 12.74;
- 15.27;
- 17.74;
- 18.96;
- 20.58;
- 20.88;
- 21.58;
- 21.78;
- 22.25;
- 22.80;
- 24.25;
- 24.66;
- 26.04;
- 26.44;
- 28.32;
- 28.96;
- 29.65;
- 30.22;
- 30.46;
- 30.78;
- 32.17;
- 33.65;
- 34.49;
- 35.08;
- 35.33;
- 37.85;
- and 38.48.
32 more elements
A crystalline compound having a structure of Formula (II)
- wherein the compound has 2θ values 8.94;
- 9.39;
- 9.76;
- 10.60;
- 11.09;
- 12.74;
- 15.27;
- 17.74;
- 18.96;
- 20.58;
- 20.88;
- 21.58;
- 21.78;
- 22.25;
- 22.80;
- 24.25;
- 24.66;
- 26.04;
- 26.44;
- 28.32;
- 28.96;
- 29.65;
- 30.22;
- 30.46;
- 30.78;
- 32.17;
- 33.65;
- 34.49;
- 35.08;
- 35.33;
- 37.85;
- and 38.48.
29 more elements
A method for the preparation of a crystalline compound of Formula (II),
- comprising (i) reacting a compound of Formula (III)
- wherein X is any suitable counterion, with a compound of Formula (IV) in an organic solvent
- (ii) preparing a solution of a compound of Formula (II) in the organic solvent;
- (iii) bringing the solution to supersaturation to permit formation of crystals;
- and (iv) isolating the crystals to provide a crystalline compound of Formula (II);
- wherein the crystalline compound has 2θ values 8.94;
- 9.39;
- 9.76;
- 10.60;
- 11.09;
- 12.74;
- 15.27;
- 17.74;
- 18.96;
- 20.58;
- 20.88;
- 21.58;
- 21.78;
- 22.25;
- 22.80;
- 24.25;
- 24.66;
- 26.04;
- 26.44;
- 28.32;
- 28.96;
- 29.65;
- 30.22;
- 30.46;
- 30.78;
- 32.17;
- 33.65;
- 34.49;
- 35.08;
- 35.33;
- 37.85;
- and 38.48.
34 more elements
Dependencies are inferred from the claim text.