IP Library › Patent Application 16124642
Patent Application
App. No. 16/124,642

STABLE COMPOSITIONS OF PEPTIDE EXPOXY KETONES

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Quick Facts
Patent No.
US None
App. No.
16/124,642
Abstract

The invention relates to pharmaceutical compositions that provide improved solubility and stability for peptide epoxy ketones. More specifically, the invention relates to pharmaceutical compositions comprising the peptide epoxy ketone proteasome inhibitor carfilzomib.

Claims (26)

1 . A pharmaceutical composition, comprising:

(i) a peptide epoxy ketone or a pharmaceutically acceptable salt thereof;

(ii) a solvent system comprising a water miscible pharmaceutically acceptable organic solvent suitable for injection selected from the group consisting of ethanol, propylene glycol, polyethylene glycol, and mixtures thereof, and optionally water; and

(iii) a non-volatile sugar acid.

2 . The pharmaceutical composition of claim 1 , wherein the non-volatile sugar acid is selected from the group consisting of lactobionic acid, glycolic acid, malic acid, citric acid, lactic acid, mandelic acid, and tartaric acid.

3 . The pharmaceutical composition of claim 2 , wherein the peptide epoxy ketone is carfilzomib or a pharmaceutically acceptable salt thereof.

4 . The pharmaceutical composition of claim 1 , wherein the solvent system comprises ethanol and propylene glycol.

5 . The pharmaceutical composition of claim 1 , wherein the solvent system comprises ethanol and polyethylene glycol.

6 . The pharmaceutical composition of claim 1 , wherein peptide epoxy ketone is carfilzomib or a pharmaceutically acceptable salt thereof and the non-volatile sugar acid is lactobionic acid.

7 . The pharmaceutical composition of claim 6 , wherein the concentration of the peptide epoxy ketone in the solvent system ranges from about 0.1 to about 10.0 mg/mL and the weight ratio of the peptide epoxy ketone to lactobionic acid ranges from about 2:1 to 15:1.

8 . The pharmaceutical composition of claim 7 , wherein the solvent system comprises ethanol, propylene glycol, and water.

9 . The pharmaceutical composition of claim 7 , wherein the solvent system comprises ethanol, polyethylene glycol, and water.

10 . The pharmaceutical composition of claim 1 comprising:

(i) carfilzomib or the pharmaceutically acceptable salt thereof;

(ii) lactobionic acid, wherein the weight ratio of the lactobionic acid to carfilzomib ranges from 2:1 to 15:1; and

(iii) a solvent system comprising ethanol, propylene glycol, and water, wherein the ethanol and propylene glycol comprise more than about 50% (v/v) of the solvent system, wherein the concentration of carfilzomib ranges from about 1 to about 6 mg/mL.

11 . The pharmaceutical composition of claim 1 comprising:

(i) Carfilzomib carfilzomib or the pharmaceutically acceptable salt thereof;

(ii) lactobioic acid, wherein the weight ratio of the lactobionic acid to carfilzomib ranges from about 4:1 to 7:1; and

(iii) a solvent system comprising ethanol, polyethylene glycol, and water, wherein the ethanol and polyethylene glycol comprise more than about 50% (v/v) of the solvent system, wherein the concentration of the carfilzomib ranges from about1 to about 6 mg/mL.

12 . A pharmaceutical composition comprising a peptide epoxy ketone and a sugar, wherein the pharmaceutical composition is lyophilized.

13 . The pharmaceutical composition of claim 12 , wherein the sugar acid is lactobionic acid.

14 . The pharmaceutical composition of claim 12 , wherein the peptide epoxy ketone is carfilzomib.

15 . The pharmaceutical composition of claim 14 , sugar acid is lactobionic acid.

16 . The pharmaceutical composition of claim 13 , wherein the weight ratio of the peptide epoxy ketone to lactobionic acid ranges from about 2:1 to 10:1.

17 . The pharmaceutical composition of claim 15 , wherein the weight ratio of the lactobionic acid to carfilzomib ranges from about 2:1 to 10:1.