IP Library › Granted Patent US 10,098,859
Granted Patent B2
US 10,098,859 · App. 14/017,879 · Granted Oct 16, 2018

Cocrystals of p-coumaric acid

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Quick Facts
Patent No.
US 10,098,859
App. No.
14/017,879
Granted
Oct 16, 2018
Kind
B2
Abstract

Disclosed herein are cocrystals of p-coumaric acid and nicotinamide. A 1:1 molar ratio and a 2:1 molar ratio of p-coumaric acid to nicotinamide are herein disclosed.

Claims (11)

1. A cocrystal of p-coumaric acid and nicotinamide having a molar ratio of p-coumaric acid to nicotinamide of 2:1 having an x-ray powder diffraction pattern comprising one or more peaks at about 16.5°2θ, about 17.6°2θ, 19.0°2θ, 22.5°2θ, about 23.0°2θ, about 23.8°2θ, about 24.8°2θ, about 27.1°2θ, or about 27.3°2θ.

2. The cocrystal of claim 1 having a DSC thermogram with an endotherm at about 174.1° C.

3. The cocrystal of claim 1 having a 13 C solid-state NMR spectrum comprising one or more peaks at about 175.4 ppm, about 172.8 ppm, about 169.8 ppm, about 158.9 ppm, about 150.0 ppm, about 148.3 ppm, about 145.2 ppm, about 138.4 ppm, about 135.0 ppm, about 128.1 ppm, about 126.4 ppm, about 124.5 ppm, about 116.9 ppm, about 115.7 ppm, or about 110.5 ppm.

4. The cocrystal of claim 2 having a 13 C solid-state NMR spectrum comprising a peak at about 158.9 ppm.

5. A pharmaceutical composition comprising at least one cocrystal of claim 1 and at least one pharmaceutically acceptable carrier.

6. The cocrystal of claim 2 having a 13 C solid state NMR spectrum comprising one or more peaks at about 175.4 ppm, about 172.8 ppm, about 169.8 ppm, about 158.9 ppm, about 150.0 ppm, about 148.3 ppm, about 145.2 ppm, about 138.4 ppm, about 135.0 ppm, about 128.1 ppm, about 126.4 ppm, about 124.5 ppm, about 116.9 ppm, about 115.7 ppm, or about 110.5 ppm..

7. A cocrystal of p-coumaric acid and nicotinamide.

8. The cocrystal of claim 7 having an x-ray powder diffraction pattern comprising one or more peaks at either (i) about 5.9°2θ, about 11.8°2θ, about 15.7°2θ, about 17.1°2θ, about 18.2°2θ, about 18.9°2θ, about 23.8°2θ, about 25.0°2θ, about 26.7°2θ, or about 28.4°2θ or (ii) about 16.5°2θ, about 17.6°2θ, about 19.0°2θ, about 22.5°2θ, about 23.0°2θ, about 23.8°2θ, about 24.8°2θ, about 27.1°2θ, or about 27.3°2θ.

9. The cocrystal of claim 8 , wherein the molar ratio of p-cournaric acid to nicotinamide is 2:1.

10. The cocrystal of claim 9 having a DSC thermogram with an endotherm at about 174° C.

11. The cocrystal of claim 9 having a 13 C solid-state NMR spectrum comprising a peak at about 158.9 ppm.

Assignments (11)
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 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 →
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 →
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 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 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 →