IP Library › Granted Patent US 10,968,192
Granted Patent B2
US 10,968,192 · App. 16/579,106 · Granted Apr 6, 2021

Crystalline solid forms of N-(1-((2-(dimethylamino)ethyl)amino)-2-methyl-1-oxopropan-2-yl)-4-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)butanamide and methods of their synthesis

Inventors: Mark Stephen Bednarz (Lower Makefield Township, PA); Kuangchu Dai (Shanghai, CN); Jeffrey Manning Eckert (Hazlet, NJ); Ngiap-Kie Lim (Dublin, CA); Lauren Sirois (San Francisco, CA); Wenxue Wu (Princeton Junction, NJ); Matthew Mangzhu Zhao (Edison, NJ)
Assignee: Lexicon Pharmaceuticals, Inc.
C07D309/10C07D207/16C07B2200/13
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Quick Facts
Patent No.
US 10,968,192
App. No.
16/579,106
Granted
Apr 6, 2021
Kind
B2
Abstract

Methods of preparing, and solid forms of N-(1-((2-(dimethylamino)ethyl)amino)-2-methyl-1-oxopropan-2-yl)-4-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)butanamide, and salts, solvates and cocrystals thereof, are disclosed.

Claims (5)

1. A crystalline form of N-(1-((2-(dimethylamino)ethyl)-amino)-2-methyl-1-oxopropan-2-yl)-4-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)butanamide L-proline:

2. The crystalline form of claim 1 having a melting point of 147±5.0° C.

3. The crystalline form of claim 2 having an X-ray powder diffraction pattern comprising peaks at one or more of 4.5, 5.3, 10.5, 12.1, 17.1, 18.8, 19.3, 22.3, 26.1, and 26.2±0.5 degrees 2θ.

4. The crystalline form of claim 1 having a melting point of 150±5.0° C.

5. The crystalline form of claim 4 having an X-ray powder diffraction pattern comprising peaks at one or more of 4.2, 7.5, 8.3, 10.9, 12.5, 14.7, 16.6, 17.7, 19.8, and 20.6±0.5 degrees 2θ.

Assignments (9)
RELEASE OF SECURITY INTEREST Recorded May 5, 2026
From: OXFORD FINANCE LLC
To: LEXICON PHARMACEUTICALS, INC.; LEXICON PHARMACEUTICALS
Reel/Frame 075545/0601 →
SECURITY INTEREST Recorded May 4, 2026
From: LEXICON PHARMACEUTICALS, INC.; LEXICON PHARMACEUTICALS (NEW JERSEY), INC.; LION ACQUISITION CORPORATION
To: HERCULES CAPITAL, INC., AS AGENT
Reel/Frame 075498/0899 →
SECURITY INTEREST Recorded Mar 17, 2022
From: LEXICON PHARMACEUTICALS, INC.
To: OXFORD FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 059432/0709 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 24, 2021
From: BEDNARZ, MARK STEPHEN
To: LEXICON PHARMACEUTICALS, INC.
Reel/Frame 055707/0295 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 2, 2021
From: ECKERT, JEFFREY MANNING; LIM, NGIAP-KIE; SIROIS, LAUREN; WU, WENXUE; ZHAO, MATTHEW MANGZHU
To: LEXICON PHARMACEUTICALS, INC.
Reel/Frame 055457/0565 →
CORRECTIVE ASSIGNMENT TO CORRECT THE INVENTOR NAME AND ASSIGNEE'S ADDRESS PREVIOUSLY RECORDED AT REEL: 054352 FRAME: 0490. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Jan 29, 2021
From: DAI, KUANGCHU
To: STA PHARMACEUTICAL HONG KONG LIMITED
Reel/Frame 055174/0522 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2020
From: LEXICON PHARMACEUTICALS (NEW JERSEY), INC.
To: LEXICON PHARMACEUTICALS, INC.
Reel/Frame 054352/0884 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2020
From: STA PHARMACEUTICAL HONG KONG LIMITED
To: LEXICON PHARMACEUTICALS (NEW JERSEY), INC.
Reel/Frame 054352/0754 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2020
From: KUANGCHU, DAI
To: STA PHARMACEUTICAL HONG KONG LIMITED
Reel/Frame 054352/0490 →
Continuity (2)
Provisional Application 62736871 · Sep 26, 2018
Related Publication 20200255394A1 · Aug 13, 2020