IP Library › Granted Patent US 9,512,166
Granted Patent B2
US 9,512,166 · App. 14/017,397 · Granted Dec 6, 2016

Cocrystals of progesterone

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Quick Facts
Patent No.
US 9,512,166
App. No.
14/017,397
Granted
Dec 6, 2016
Kind
B2
Abstract

Disclosed herein are cocrystals of progesterone and a coformer containing a six-membered aromatic ring having at least one substituent possessing a carbonyl functionality. Cocrystals of progesterone and a coformer selected from vanillic acid, benzoic acid, salicylic acid, cinnamic acid, or vanillin are also disclosed herein.

Claims (9)

1. A hemihydrate cocrystal of progesterone and benzoic acid in a molar ratio of 2:1 progesterone to benzoic acid having an x-ray powder diffraction pattern having one or more peaks at about 8.1, 12.3, 13.8, 14.4, 16.9, 18.0, 20.7, or 21.1 °2θ.

2. The cocrystal of claim 1 having a DSC thermogram with an endotherm at about 96° C.

3. A cocrystal of progesterone and salicylic acid in a molar ratio of 1:1 progesterone to salicylic acid having an x-ray powder diffraction pattern having one or more peaks at about 6.7, 10.7, 13.3, 13.5, 14.3, 14.7, 17.7, 20.2, 20.5, or 27.0 °2θ.

4. The cocrystal of claim 3 having a DSC thermogram with an endotherm at about 88° C.

5. A cocrystal of progesterone and salicylic acid in a molar ratio of 2:1 progesterone to salicylic acid having an x-ray powder diffraction pattern having one or more peaks at about 8.3, 13.4, 13.8, 14.0, 14.6, 16.9, 17.7, 18.1, 20.2, 20.6 or 27.0 °2θ.

6. A. cocrystal of progesterone and vanillin in a molar ratio of 2:1 progesterone to vanillin having an x-ray powder diffraction pattern having one or more peaks at about 8.4, 10.5, 12.4, 13.1, 13.3, 15.2, 15.8, 15.9, 17.5, 19.0, 19.5, 19.8, 20.0, 20.8, 22.9, or 25.8 °2θ.

7. The cocrystal of claim 6 having a DSC thermogram with an endotherm at about 97° C.

8. A pharmaceutical composition comprising one or more cocrystals selected from (i) a cocrystal of progesterone and vanillin in a molar ratio of 2:1 progesterone to vanillin having an x-ray powder diffraction pattern having one or more peaks at about 8.4, 10.5, 12.4, 13.1, 13.3, 15.2, 15.8, 15.9, 17.5, 19.0, 19.5, 19.8, 20.0, 20.8, 22.9, or 25.8 °2θ, (ii) a hemihydrate cocrystal of progesterone and benzoic acid in a molar ratio of 2:1 progesterone to benzoic acid having an x-ray powder diffraction pattern having one or more peaks at about 8.1, 12.3, 13.8, 14.4, 16.9, 18.0, 20.7, or 21.1 °θ; and at least one pharmaceutically acceptable carrier.

9. A method of supplementing progesterone in women comprising administering to a patient in need thereof the pharmaceutical composition of claim 8 .

Assignments (17)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2025
From: CURIA INDIANA, LLC
To: CURIA GLOBAL, INC.
Reel/Frame 073047/0677 →
CHANGE OF NAME Recorded May 20, 2025
From: AMRI SSCI, LLC
To: CURIA INDIANA, LLC
Reel/Frame 071298/0518 →
ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY, RECORDED ON MARCH 16, 2023, AT REEL/FRAME 063008/0046 Recorded Mar 17, 2025
From: BARCLAYS BANK PLC, AS EXISTING AGENT
To: APOLLO ADMINISTRATIVE AGENCY LLC, AS SUCCESSOR AGENT
Reel/Frame 070531/0241 →
ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY, RECORDED ON SEPTEMBER 1, 2017, AT REEL/FRAME 043746/0621 Recorded Mar 17, 2025
From: BARCLAYS BANK PLC, AS EXISTING AGENT
To: APOLLO ADMINISTRATIVE AGENCY LLC, AS SUCCESSOR AGENT
Reel/Frame 070531/0279 →
SECURITY INTEREST Recorded Mar 16, 2023
From: CURIA INDIANA, LLC (F/K/A AMRI SSCI, LLC)
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 063008/0046 →
SECURITY INTEREST Recorded Mar 16, 2023
From: CURIA INDIANA, LLC (F/K/A AMRI SSCI, LLC)
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 063008/0185 →
SECURITY INTEREST Recorded Sep 6, 2021
From: CURIA GLOBAL, INC. (FKA ALBANY MOLECULAR RESEARCH, INC.); CURIA MASSACHUSETTS, INC. (FKA AMRI BURLINGTON, INC.); CURIA WISCONSIN, INC. (FKA CEDARBURG PHARMACEUTICALS, INC.); CURIA INDIANA, LLC (FKA AMRI SSCI, LLC); CURIA NEW MEXICO, LLC (FKA OSO BIOPHARMACEUTICALS MANUFACTURING, LLC); CURIA IP HOLDINGS, LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 057423/0665 →
RELEASE OF SECURITY INTEREST Recorded Oct 29, 2020
From: MORGAN STANLEY SENIOR FUNDING, INC., AS COLLATERAL AGENT
To: ALBANY MOLECULAR RESEARCH, INC.; AMRI BURLINGTON, INC.; CEDARBURG PHARMACEUTICALS, INC.; EUTICALS INC.; OSO BIOPHARMACEUTICALS MANUFACTURING, LLC
Reel/Frame 054252/0687 →
FIRST LIEN SECURITY AGREEMENT Recorded Sep 1, 2017
From: ALBANY MOLECULAR RESEARCH, INC.; AMRI BURLINGTON, INC.; CEDARBURG PHARMACEUTICALS, INC.; EUTICALS INC.; OSO BIOPHARMACEUTICALS MANUFACTURING, LLC-BY ITS SOLE MEMBER: ALO ACQUISITION LLC
To: BARCLAYS BANK, PLC AS COLLATERAL AGENT
Reel/Frame 043746/0621 →
SECOND LIEN SECURITY AGREEMENT Recorded Sep 1, 2017
From: ALBANY MOLECULAR RESEARCH, INC.; AMRI BURLINGTON, INC.; CEDARBURG PHARMACEUTICALS, INC.; EUTICALS INC.; OSO BIOPHARMACEUTICALS MANUFACTURING LLC-BY ITS SOLE MEMBER:ALO ACQUISITION LLC
To: MORGAN STANLEY SENIOR FUNDING, INC.
Reel/Frame 043746/0657 →
RELEASE OF SECURITY INTEREST Recorded Aug 31, 2017
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: ALBANY MOLECULAR RESEARCH, INC.; ALO ACQUISITION LLC; AMRI BURLINGTON, INC.; AMRI RENSSELAER, INC.; CEDARBURG PHARMACEUTICALS, INC.; OSO BIOPHARMACEUTICALS MANUFACTURING, LLC; AMRI SSCI, LLC; EUTICALS INC.
Reel/Frame 043742/0085 →
SECURITY INTEREST Recorded Aug 5, 2015
From: ALBANY MOLECULAR RESEARCH, INC.; AMRI SSCI, LLC
To: BARCLAYS BANK PLC, AS THE COLLATERAL AGENT
Reel/Frame 036257/0914 →
SECURITY INTEREST Recorded May 26, 2015
From: AMRI SSCI, LLC
To: BARCLAYS BANK PLC, AS THE COLLATERAL AGENT
Reel/Frame 035710/0880 →
CHANGE OF NAME Recorded Apr 23, 2015
From: AMRI AMERICIUM, LLC
To: AMRI SSCI, LLC
Reel/Frame 035487/0184 →
ASSIGNMENT EFFECTIVE 13 FEB 2015 Recorded Apr 23, 2015
From: APTUIT (WEST LAFAYETTE), LLC
To: AMRI AMERICIUM, LLC
Reel/Frame 035492/0830 →
CORRECTIVE ASSIGNMENT TO CORRECT THE TO RE-RECORD IN DOC. ID # 502826208 ASSIGNEE'S NAME FROM APTUIT INC. TO APTUIT (WEST LAFAYETTE) LLC PREVIOUSLY RECORDED ON REEL 031136 FRAME 0134. ASSIGNOR(S) HEREBY CONFIRMS THE APTUIT (WEST LAFAYETTE) LLC. Recorded Jun 10, 2014
From: ALBERT, EKATERINA; ANDRES, PATRICIA; BEVILL, MELANIE JANELLE; SMIT, JARED; NELSON, JENNIFER
To: APTUIT (WEST LAFAYETTE) LLC
Reel/Frame 033115/0890 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 4, 2013
From: ALBERT, EKATERINA; ANDRES, PATRICIA; BEVILL, MELANIE JANELLE; SMIT, JARED; NELSON, JENNIFER
To: APTUIT, INC.
Reel/Frame 031136/0134 →