IP Library Granted Patent US 10,639,375
Granted Patent B2
US 10,639,375 · App. 16/037,452 · Granted May 5, 2020

Progesterone formulations

Inventors: Brian A. Bernick (Boca Raton, FL); Julia M. Amadio (Boca Raton, FL); Peter H. R. Persicaner (Boca Raton, FL); Janice Louise Cacace (Miami, FL); Thorsteinn Thorsteinsson (West Palm Beach, FL); Frederick D. Sancilio (Palm Beach Gardens, FL); Neda Irani (Palm Beach Gardens, FL)
Assignee: TherapeuticsMD, Inc.
A61K47/14A61K9/0014A61K9/1075A61K9/48A61K9/4825A61K31/565A61K31/566A61K31/57A61K31/573A61K45/06A61K47/10
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Quick Facts
Patent No.
US 10,639,375
App. No.
16/037,452
Granted
May 5, 2020
Kind
B2
Abstract

Various pharmaceutical formulations are disclosed herein. For example, a pharmaceutical formulation is disclosed comprising ultra-micronized progesterone.

Claims (27)

1. A pharmaceutical composition comprising:

progesterone and an effective amount of estradiol not exceeding 2 mg, wherein the estradiol and progesterone are present in a weight ratio of 1:100;

a medium chain oil; and

a non-ionic surfactant;

further wherein the progesterone is present from about 20 to about 50 weight percent of the composition.

2. The pharmaceutical composition of claim 1 , wherein a portion of the progesterone is solubilized and a portion of the progesterone is suspended.

3. The pharmaceutical composition of claim 1 , wherein the non-ionic surfactant is selected from the group consisting of lauroyl macrogol-32 glycerides EP, lauroyl polyoxyl-32 glycerides, and caprylocaproyl macrogol-8 glycerides EP.

4. The pharmaceutical composition of claim 1 , wherein the composition is provided in a gelatin capsule.

5. The pharmaceutical composition of claim 1 , wherein the composition provides increased progesterone bioavailability compared to a micronized progesterone suspended in peanut oil.

6. The pharmaceutical composition of claim 1 , wherein the medium chain oil comprises at least one C6-C14 fatty acid mono-, di-, or tri-ester of glycerol or mono- or di-ester of a glycol.

7. The pharmaceutical composition of claim 6 , wherein the at least one C6-C14 fatty acid mono-, di-, or tri-ester of glycerol is a C8 fatty acid mono-, di-, or tri-ester of glycerol.

8. The pharmaceutical composition of claim 6 , further comprising a second C6-C14 fatty acid mono-, di-, or tri-ester of glycerol.

9. The pharmaceutical composition of claim 8 , wherein the second C6-C14 fatty acid mono-, di-, or tri-ester of glycerol is a C10 fatty acid mono-, di-, or tri-ester of glycerol.

10. The pharmaceutical composition of claim 9 , wherein the medium chain oil is CAPMUL MCM.

11. The pharmaceutical composition of claim 1 , comprising 50 mg of progesterone.

12. The pharmaceutical composition of claim 1 , comprising 100 mg of progesterone.

13. The pharmaceutical composition of claim 12 , wherein the progesterone is ultra-micronized and has an X50 less than or equal to 15 microns.

14. The pharmaceutical composition of claim 13 , wherein the ultra-micronized progesterone has an X90 of less than about 25 microns.

15. The pharmaceutical composition of claim 12 , wherein a portion of the progesterone is solubilized and a portion of the progesterone is suspended.

16. The pharmaceutical composition of claim 15 , wherein the non-ionic surfactant is selected from the group consisting of lauroyl macrogol-32 glycerides EP, lauroyl polyoxyl-32 glycerides, and caprylocaproyl macrogol-8 glycerides EP.

17. The pharmaceutical composition of claim 16 , wherein the composition is provided in a gelatin capsule.

18. The pharmaceutical composition of claim 16 , wherein the composition provides increased progesterone bioavailability compared to a micronized progesterone suspended in peanut oil.

19. The pharmaceutical composition of claim 18 , wherein the medium chain oil comprises at least one C6-C14 fatty acid mono-, di-, or tri-ester of glycerol or mono- or di-ester of a glycol.

20. The pharmaceutical composition of claim 19 , wherein the at least one C6-C14 fatty acid mono-, di-, or tri-ester of glycerol is a C8 fatty acid mono-, di-, or tri-ester of glycerol.

21. The pharmaceutical composition of claim 20 , further comprising a second C6-C14 fatty acid mono-, di-, or tri-ester of glycerol.

22. The pharmaceutical composition of claim 21 , wherein the second C6-C14 fatty acid mono-, di-, or tri-ester of glycerol is a C10 fatty acid mono-, di-, or tri-ester of glycerol.

23. The pharmaceutical composition of claim 22 , wherein the medium chain oil is CAPMUL MCM.

Assignments (8)
TERMINATION AND RELEASE OF GRANT OF A SECURITY INTEREST - PATENTS Recorded Dec 30, 2022
From: SIXTH STREET SPECIALTY LENDING, INC. (F/K/A TPG SPECIALTY LENDING, INC.)
To: THERAPEUTICSMD, INC.
Reel/Frame 062254/0813 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NO. 16/401,844 PREVIOUSLY RECORDED AT REEL: 050928 FRAME: 0987. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF ADDRESS. Recorded Sep 24, 2021
From: THERAPEUTICSMC, INC.
To: THERAPEUTICSMD, INC.
Reel/Frame 057698/0571 →
SECURITY INTEREST Recorded Jan 27, 2021
From: THERAPEUTICSMD, INC.
To: SIXTH STREET SPECIALTY LENDING, INC. (F/K/A TPG SPECIALTY LENDING, INC.)
Reel/Frame 055049/0651 →
SECURITY INTEREST Recorded Sep 18, 2020
From: THERAPEUTICSMD, INC.
To: SIXTH STREET SPECIALTY LENDING, INC. (F/K/A TPG SPECIALTY LENDING, INC.)
Reel/Frame 053820/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2020
From: IRANI, NEDA
To: THERAPEUTICSMD, INC.
Reel/Frame 051532/0277 →
CHANGE OF ADDRESS Recorded Nov 5, 2019
From: THERAPEUTICSMD, INC.
To: THERAPEUTICSMD, INC.
Reel/Frame 050928/0987 →
PATENT SECURITY AGREEMENT Recorded Apr 24, 2019
From: THERAPEUTICSMD, INC.
To: TPG SPECIALTY LENDING, INC.
Reel/Frame 048990/0820 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2019
From: AMADIO, JULIA M.; BERNICK, BRIAN; CACACE, JANICE LOUISE; PERSICANER, PETER H. R.; SANCILIO, FREDERICK D.; THORSTEINSSON, THORSTEINN
To: THERAPEUTICSMD, INC.
Reel/Frame 048715/0152 →