IP Library Granted Patent US 10,556,922
Granted Patent B2
US 10,556,922 · App. 15/764,100 · Granted Feb 11, 2020

Crystalline and amorphous forms of 17-alpha-hydroxyprogesterone caproate

Inventor: Mahmoud Mirmehrabi (Halifax, CA)
Assignee: AMAG PHARMACEUTICALS, INC.
C07J7/0045A61K9/10A61K31/56A61K47/44A61P43/00A61K9/0014A61K9/0019A61K9/0053C07B2200/13
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Quick Facts
Patent No.
US 10,556,922
App. No.
15/764,100
Granted
Feb 11, 2020
Kind
B2
Abstract

The disclosure is in part directed to crystalline forms of 17-α-hydroxyprogesterone caproate and variants thereof.

Claims (22)

1. A crystalline form of 17-α-hydroxyprogesterone caproate characterized by a powder X-ray diffraction pattern having a characteristic peak in degrees 2θ at about 9.6, 12.2, and 18.3 and a differential scanning calorimetry endothermic peak at about 100-105° C.

2. The crystalline form of claim 1 , characterized by a powder X-ray diffraction pattern having characteristic peaks in degrees 2θ at about 9.6, 12.2, 13.9, 14.8, 15.4, 18.3, and 19.2.

3. The crystalline form of claim 1 , characterized by a powder X-ray diffraction pattern having characteristic peaks in degrees 2θ at 9.6, 12.2, 13.0, 13.9, 14.8, 15.4, 18.3, and 19.2.

4. The crystalline form of claim 1 , having the powder X-ray diffraction pattern shown in FIG. 4 .

5. The crystalline form of claim 1 , wherein the powder X-ray diffraction pattern was obtained using Cu Kα radiation.

6. A pharmaceutical composition comprising the crystalline form of claim 1 , and a pharmaceutically acceptable excipient.

7. The pharmaceutical composition of claim 6 , wherein the composition is a formulation for subcutaneous or intramuscular injections.

8. The pharmaceutical composition of claim 6 , wherein the composition is a formulation for oral administration.

9. The pharmaceutical composition of claim 6 , wherein the composition is a formulation for topical administration.

10. The pharmaceutical composition of claim 6 , wherein the composition is a formulation for rectal or vaginal administration.

11. The pharmaceutical composition of claim 6 , wherein the composition is a suspension of the crystalline form.

12. A drug substance comprising at least a detectable amount of the crystalline form of claim 1 .

13. A drug substance comprising substantially pure crystalline form of claim 1 .

14. The drug substance of claim 12 , further comprising a crystalline form of 17-α-hydroxyprogesterone caproate characterized by a powder X-ray diffraction pattern having a characteristic peak in degrees 2θ at about 7.3.

15. A crystalline form of 17-α-hydroxyprogesterone caproate characterized by a powder X-ray diffraction pattern having a characteristic peak in degrees 2θ at about 9.6, 12.2, 13.9, 14.8, 15.4, 18.3, and 19.2.

16. A pharmaceutical composition comprising the crystalline form of claim 15 , and a pharmaceutically acceptable excipient.

17. The pharmaceutical composition of claim 16 , wherein the composition is a formulation for subcutaneous or intramuscular injections.

18. The pharmaceutical composition of claim 16 , wherein the composition is a formulation for oral administration.

19. The pharmaceutical composition of claim 16 , wherein the composition is a formulation for topical, rectal or vaginal administration.

20. The pharmaceutical composition of claim 16 , wherein the composition is a suspension of the crystalline form.

21. A drug substance comprising at least a detectable amount of the crystalline form of claim 15 .

22. A drug substance comprising substantially pure crystalline form of claim 15 .

Assignments (9)
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 17, 2025
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: COVIS PHARMA GMBH
Reel/Frame 070537/0122 →
RELEASE OF SECURITY INTEREST Recorded Jun 2, 2023
From: BARCLAYS BANK PLC
To: COVIS PHARMA GMBH
Reel/Frame 063841/0208 →
RELEASE OF SECURITY INTEREST Recorded Feb 18, 2022
From: CAPITAL ONE, NATIONAL ASSOCIATION
To: COVIS PHARMA GMBH
Reel/Frame 059043/0226 →
NOTICE OF GRANT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY (SECOND LIEN) Recorded Feb 18, 2022
From: COVIS PHARMA GMBH
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 059232/0514 →
NOTICE OF GRANT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY (FIRST LIEN) Recorded Jan 4, 2022
From: COVIS PHARMA GMBH
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 058640/0787 →
CORRECTIVE ASSIGNMENT TO CORRECT THE CORRESPONDENCE ADDRESS PREVIOUSLY RECORDED AT REEL: 055241 FRAME: 0517. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Feb 23, 2021
From: AMAG PHARMACEUTICALS, INC.
To: COVIS PHARMA GMBH
Reel/Frame 055363/0746 →
SECURITY INTEREST Recorded Feb 22, 2021
From: COVIS PHARMA GMBH
To: CAPITAL ONE, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 055354/0063 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2021
From: AMAG PHARMACEUTICALS, INC.
To: COVIS PHARMA GMBH
Reel/Frame 055241/0517 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2018
From: MIRMEHRABI, MAHMOUD
To: AMAG PHARMACEUTICALS, INC.
Reel/Frame 045599/0784 →
Cited By (1)
US 12,502,396