IP Library Granted Patent US 10,000,464
Granted Patent B2
US 10,000,464 · App. 15/336,143 · Granted Jun 19, 2018

Process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4H-imidazo[1,2-A][1,4]benzodiazepine-4-yl]propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process

Inventors: Gary Stuart Tilbrook (Huntingdon, GB); Andreas Schumacher (Efringen-Kirchen, DE); Rene Emmenegger (Basel, CH)
Assignee: PAION UK LIMITED
C07D401/04C07D213/40C07D213/50C07D487/04C07F9/65586
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Quick Facts
Patent No.
US 10,000,464
App. No.
15/336,143
Granted
Jun 19, 2018
Kind
B2
Abstract

The invention concerns a new process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4H-imidazo[1,2-a][1,4]benzodiazepine-4-yl]-propionic acid methyl ester or 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4H-imidazo[1,2-a][1,4]benzodiazepine-4-yl]propionic acid methyl ester benzene sulfonate (P) which comprises reacting 3-[(S)-7-bromo-2-((R and/or S)-2-hydroxy-propylamino)-5-pyridin-2-yl-3H-benzo[e][1,4]diazepin-3-yl]-propionic acid methyl ester of formula (EM) with an oxidizing agent and optionally treating the reaction product under acidic conditions, such as to produce the compound of formula (F) or the compound (P), and new compounds useful as starting materials or as intermediates for performing that process.

Claims (10)

1. A salt of a compound of the formula

2. The salt according to claim 1 , wherein said salt is a hydrochloride salt.

3. A process for preparing a salt of a compound of the formula

wherein R is hydrogen, comprising reacting a compound of the formula wherein R is —C(O)O-tBu with an acid.

4. The process according to claim 3 , wherein said acid is hydrochloric acid.

5. The process according to claim 3 , wherein said salt is a hydrochloride salt.

6. A process for preparing a compound of the formula

comprising reacting a compound of the formula

with an acid.

7. The process according to claim 6 , wherein said acid is hydrochloric acid.

Assignments (3)
CHANGE OF ADDRESS Recorded Dec 5, 2022
From: PAION UK LIMITED
To: PAION UK LIMITED
Reel/Frame 062063/0061 →
CHANGE OF ADDRESS Recorded Nov 30, 2022
From: TILBROOK, GARY STUART; SCHUMACHER, ANDREAS; EMMENEGGER, RENÉ
To: PAION UK LIMITED
Reel/Frame 062019/0907 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2017
From: TILBROOK, GARY STUART; SCHUMACHER, ANDREAS; EMMENEGGER, RENE
To: PAION UK LIMITED
Reel/Frame 040935/0735 →
Priority Claims (1)
EP 09011914 · Sep 18, 2009 · regional
Continuity (3)
Continuation 14841899 · Sep 1, 2015
Division 13496742
Related Publication 20170044135A1 · Feb 16, 2017