IP Library Granted Patent US 11,020,486
Granted Patent B2
US 11,020,486 · App. 15/032,773 · Granted Jun 1, 2021

Sesame oil based injection formulations

Inventors: Joseph M. Beaurline (St. Paul, MN); James M. Elvecrog (St. Paul, MN); John P. Vasilakos (St. Paul, MN); John Thomas Capecchi (St. Paul, MN); Karen Elizabeth Johnson (St. Paul, MN)
Assignee: 3M INNOVATIVE PROPERTIES COMPANY
A61K47/44A61K9/0019A61K31/4745A61K47/10C07D471/04
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Quick Facts
Patent No.
US 11,020,486
App. No.
15/032,773
Granted
Jun 1, 2021
Kind
B2
Abstract

Injectable formulations comprising ethanol, sesame oil, and an Immune Response Modifier compound are disclosed. Methods of making the formulations and methods of using the formulations for treatment of a disease in a subject, e.g., neoplastic disease, comprising injecting the formulations into a subject hi need of treatment, are also provided.

Claims (18)

1. An intratumoral injectable pharmaceutical formulation, comprising:

sesame oil having a hydroxyl value less than or equal to 2, an acid value less than or equal to 0.1, and a peroxide value less than or equal to 1;

ethanol; and

an immune response modifier compound, wherein the immune response modifier compound is N-(4-{[4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxy}butyl)octadecanamide, or a pharmaceutically acceptable salt thereof,

wherein the ethanol is present in a concentration of from about 1 wt-% to about 9 wt-%.

2. The formulation according to claim 1 , wherein the ethanol is present in a concentration of from about 3 wt-% to about 8 wt-%.

3. The formulation according to claim 1 , wherein the ethanol is present in a concentration of from about 6.5 wt-% to about 7.5 wt-%.

4. The formulation according to claim 1 , wherein the immune response modifier compound is present in a concentration of from about 0.1 mg/mL to about 10 mg/mL.

5. The formulation according to claim 1 , wherein the total nitrogen content of the sesame oil is less than or equal to 1 ppm.

6. The formulation according to claim 1 , wherein the sesame oil contains no more than 0.05 wt-% of sesamin and no more than 0.05 wt-% of sesamolin.

7. The formulation of claim 1 , wherein the formulation comprises:

7.5 wt-% ethanol;

300 ppm butylated hydroxyanisole (BHA); and

from 0.1 mg/mL to about 2.5 mg/mL N-(4-{[4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxy}butyl)octadecanamide.

8. An intratumoral injectable pharmaceutical formulation, comprising sesame oil having a hydroxyl value less than or equal to 2, an acid value less than or equal to 0.1, and a peroxide value less than or equal to 1, and ethanol; and an immune response modifier compound, wherein the immune response modifier compound is N-(4-{[4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxy}butyl)octadecanamide or a pharmaceutically acceptable salt thereof, wherein the composition is not aqueous.

9. The formulation of claim 1 , wherein the sesame oil has a total nitrogen content of less than or equal to 1 ppm.

10. The formulation of claim 1 , wherein the sesame oil contains no more than 0.05 wt-% of sesamin.

11. The formulation of claim 1 , wherein the sesame oil contains no more than 0.05 wt-% of sesamolin.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2024
From: 3M INNOVATIVE PROPERTIES COMPANY
To: SOLVENTUM INTELLECTUAL PROPERTIES COMPANY
Reel/Frame 066430/0295 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2016
From: BEAURLINE, JOSEPH; ELVECROG, JAMES; VASILAKOS, JOHN; CAPECCHI, JOHN T; JOHNSON, KAREN E
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 038600/0373 →