US 12,144,817 B2
Testosterone ester triglyceride formulations
Shaowei Ong, Ewing, NJ (US)
Assigned to Antares Pharma, Inc., Ewing, NJ (US)
Filed by Antares Pharma, Inc., Ewing, NJ (US)
Filed on Aug. 18, 2021, as Appl. No. 17/405,984.
Application 17/405,984 is a continuation of application No. 16/847,067, filed on Apr. 13, 2020, granted, now 11,123,352.
Application 16/847,067 is a continuation of application No. 16/117,963, filed on Aug. 30, 2018, granted, now 10,646,495, issued on May 12, 2020.
Claims priority of provisional application 62/552,190, filed on Aug. 30, 2017.
Prior Publication US 2022/0079955 A1, Mar. 17, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 47/44 (2017.01); A61K 9/00 (2006.01); A61K 9/10 (2006.01); A61K 9/107 (2006.01); A61K 31/5685 (2006.01); A61K 47/14 (2017.01)
CPC A61K 31/5685 (2013.01) [A61K 9/0019 (2013.01); A61K 9/10 (2013.01); A61K 9/107 (2013.01); A61K 47/14 (2013.01); A61K 47/44 (2013.01)] 16 Claims
 
1. A light stable testosterone ester pharmaceutical formulation for parenteral administration comprising a testosterone ester of Formula 1, a pharmaceutically acceptable carrier comprising a triglyceride of Formula 2, and a testosterone ester adduct of Formula 3:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein in Formula 1 and Formula 2:
R1 is an alkyl or alkenyl substituent; and
each of R2, R3, and R4 is an acyl group corresponding to a fatty acid selected from the group consisting of linoleic acid, oleic acid, palmitic acid, ricinoleic acid, linolenic acid, and stearic acid;
wherein in Formula 3:
R1 is an alkyl or alkenyl substituent as defined in Formula 1;
R5 is an acyl group corresponding to an unsaturated fatty acid;
G is a glycerol, or monoglyceride, or diglyceride residue;
n is 1, 2, or 3; and
the testosterone residue is connected to an allylic or doubly allylic carbon of R5;
wherein the light stability of the pharmaceutical formulation is assessed a period of time after making the formulation by measuring a concentration of available testosterone ester and comparing it to an initial testosterone ester concentration in the pharmaceutical formulation, and by measuring a concentration of between 0.005 mg/ml and 25 mg/ml of the testosterone ester adduct of Formula 3.