IP Library › Granted Patent US 12,344,596
Granted Patent B2
US 12,344,596 · App. 18/114,104 · Granted Jul 1, 2025

Solid forms of (S)-1-((2′,6-bis(difluoromethyl)-[2,4′-bipyridin]-5-yl)oxy)-2,4-dimethylpentan-2-amine and salts thereof

Inventors: Qun Li (Newark, DE); Wenxue Wu (Princeton Junction, NJ); Matthew Mangzhu Zhao (Edison, NJ)
Assignee: LEXICON PHARMACEUTICALS, INC.
C07D401/04A61K9/28A61K31/444A61P29/00C07B2200/13
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Quick Facts
Patent No.
US 12,344,596
App. No.
18/114,104
Granted
Jul 1, 2025
Kind
B2
Abstract

Salts of the AAK1 inhibitor (S)-1-((2′,6-bis(difluoromethyl)-[2,4′-bipyridin]-5-yl)oxy)-2,4-dimethylpentan-2-amine and solid forms thereof are disclosed, as are pharmaceutical formulations comprising them and methods of their preparation.

Claims (12)

1. A crystalline compound, which is crystalline(S)-1-((2′,6-bis(difluoromethyl)-[2,4′-bipyridin]-5-yl)oxy)-2,4-dimethylpentan-2-aminium dihydrogen phosphate (Compound K):

having an XPRD pattern comprising peaks at one or more of about 4.81, 5.99, 7.44, 7.89, 11.66, 14.85, 15.77, 19.19, 20.86, 21.65, 23.96, 24.48, or 24.73 degrees 2-theta.

2. The crystalline compound of claim 1 , which has a melting point of about 184° C.

3. A composition comprising an active pharmaceutical ingredient (API), an excipient, and a lubricant, wherein the API is the crystalline compound of claim 1 .

4. The composition of claim 3 , which comprises less than 0.05 weight percent of at least one of: 2′,6-bis(difluoromethyl)-5-fluoro-2,4′-bipyridine; 5-(tert-butoxy)-2′,6-bis(difluoromethyl)-5-fluoro-2,4′-bipyridine: (S)-2-((2′,6-bis(difluoromethyl)-[2,4′-bipyridin]-5-yl)oxy)-2-phenylacetic acid; (S)-1-((2′,6-bis(difluoromethyl)-[2,4′-bipyridin]-5-yl)oxy)-2,4-dimethylpentan-2-amine; or(S)-1-((5′-(((S)-2-amino-2,4-dimethylpentyl)oxy)-6-6′-bis(difluoromethyl)-[2,2′-bipyridin]-5-yl)oxyl)-2-methylhexan-2-amine the compounds listed in Table 2.

5. A tablet comprising the composition of claim 3 .

6. The tablet of claim 5 , which is coated.

7. The tablet of claim 5 , which comprises 10, 20, or 50 mg of the API.

8. A method of treating or managing pain in a patient, which comprises administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1 .

9. A method of treating or managing pain in a patient, which comprises administering to a patient in need thereof a therapeutically effective amount of the composition of claim 3 .

10. The method of claim 8 , wherein the pain is neuropathic pain.

11. The method of claim 9 , wherein the pain is neuropathic pain.

Assignments (7)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 3, 2023
From: WU, WENXUE; ZHAO, MATTHEW MANGZHU
To: LEXICON PHARMACEUTICALS, INC.
Reel/Frame 064138/0227 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 3, 2023
From: LEXICON PHARMACEUTICALS (NEW JERSEY), INC.
To: LEXICON PHARMACEUTICALS, INC.
Reel/Frame 064138/0278 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2023
From: WILMINGTON PHARMATECH
To: LEXICON PHARMACEUTICALS (NEW JERSEY), INC.
Reel/Frame 064135/0598 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2023
From: LI, QUN
To: WILMINGTON PHARMATECH
Reel/Frame 064117/0812 →
AMENDMENT TO PREVIOUSLY FILED SECURITY INTEREST Recorded May 17, 2023
From: LEXICON PHARMACEUTICALS, INC.
To: OXFORD FINANCE LLC
Reel/Frame 063666/0326 →
Continuity (2)
Provisional Application 63315507 · Mar 1, 2022
Related Publication 20230357182A1 · Nov 9, 2023
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