IP Library Granted Patent US 9,126,936
Granted Patent B2
US 9,126,936 · App. 13/957,694 · Granted Sep 8, 2015

Process for synthesizing oxidized lactam compounds

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Quick Facts
Patent No.
US 9,126,936
App. No.
13/957,694
Granted
Sep 8, 2015
Kind
B2
Abstract

The invention provides a method for the synthesis of dehydrogenated lactam drugs of Formula I:

Claims (5)

1. A method for preparing a compound of Formula VI, comprising the step of reacting a compound of Formula VIA with a compound of Formula II in the presence of an acid:

wherein each R A , R B , R C , and R D is independently selected from hydrogen, halogen, —CN, NH 2 , NR 100 R 101 , SR 100 , OR 100 , aliphatic, substituted aliphatic, aryl and substituted aryl; wherein R 100 and R 101 , are independently selected from hydrogen, halogen, aliphatic, substituted aliphatic, aryl or substituted aryl.

2. The method according to claim 1 , wherein said compound of Formula II is selected from 3,4-dichloro-5,6-dicyano-1,4-benzoquinone, 3,4,5,6-tetrachloro-1,2-benzquinone, ortho-benzoquinone and para-benzoquinone.

3. The method according to claim 1 , wherein said acid is selected from trifluroacetic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, chlorosulfonic acid, dichloroacetic acid, trichloroacetic acid, acetic acid, propionic acid, sulfuric acid, phosphoric acid, nitric acid, camphorsulfonic acid, hydrochloric acid, oxalic acid, formic acid, propanoic acid, butanoic acid, pentanoic acid, benzoic acid, pyruvic acid, malonic acid, succinic acid, glutaric acid, fumaric acid, citric acid, ascorbic acid, tartaric acid, maleic acid, and hydrobromic acid, and mixtures thereof.

4. The method according to claim 1 , wherein the reaction is conducted in a solvent selected from tetrahydrofuran, tert-butylmethylether, dimethoxy-ethane, dioxane, benzene, toluene, xylene, dimethylformamide, acetone, acetonitrile, chloroform, dichloromethane, 1,2-dichloroethane, ethyl acetate, n-propyl acetate, isopropyl acetate, methyl-t-butyl ether, methyl butyl ketone and combinations thereof.

Assignments (3)
SECURITY INTEREST Recorded Feb 13, 2026
From: ALKERMES PHARMA IRELAND LIMITED
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 074858/0405 →
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (073213/0302) Recorded Feb 13, 2026
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: ALKERMES PHARMA IRELAND LIMITED
Reel/Frame 074858/0429 →
SECURITY INTEREST Recorded Oct 23, 2025
From: ALKERMES PHARMA IRELAND LIMITED
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 073213/0302 →