Optically active 5H-pyrrolo[3,4-b]pyrazine derivative, its preparation and pharmaceutical compositions containing it

• US 6,444,673 B1
• Filed: 11/28/2000
• Issued: 09/03/2002
• Est. Priority Date: 01/17/1991
• Status: Expired due to Term

• Current Assignee: Sunovion Pharmaceuticals Inc. (Sumitomo Chemical Company Limited)
• Original Assignee: Sepracor Incorporated
• Inventors: Cotrel, Claude, Roussel, Gérard
• Primary Examiner(s): Berch, Mark L
• Application Number:
  US09/722,438
• Time in Patent Office: 644 Days
• Field of Search: 544/350, 514/249
• US Class Current: 514/249
• CPC Class Codes: A61P 25/08 Antiepileptics; Anticonvulsants
• CPC Class Codes: A61P 25/20 Hypnotics; Sedatives
• CPC Class Codes: C07D 487/04 Ortho-condensed systems

Abstract

Dextrorotatory isomer of 6-(5-chloro-2-pyridyl)-5-[(4-methyl-1-piperazinyl)carbonyloxy]-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine, its preparation and pharmaceutical compositions containing it which are usable as tranquillizers and hypnotics.

Claims

1. 6-(5-chloro-2-pyridyl)-5-[(4-methyl-1-piperazinyl)carbonyloxy]-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine, or a pharmaceutically acceptable salt thereof, in the form of its dextrorotatory isomer and essentially free of its levorotatory isomer.

3. The compound according to claim 1, wherein the pharmaceutically acceptable salt is a salt of a mineral acid, or a substituted derivative thereof, selected from the group consisting of hydrochlorides, sulfates, nitrates, and phosphates.

4. The compound according to claim 1, wherein the pharmaceutically acceptable salt is a salt of an organic acid, or a substituted derivative thereof, selected from the group consisting of acetates, propionates, succinates, benzoates, fumarates, tartrates, theophyllineacetates, salicylates, and phenolphthalinates.

2. A pharmaceutical composition comprising an effective amount of the dextrorotatory isomer, essentially free of the levorotatory isomer of 6-(5-chloro-2-pyridyl)-5-[(4-methyl-1-piperazinyl)-carbonyloxy]-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

5. The pharmaceutical composition according to claim 2, wherein the pharmaceutically acceptable salt is a salt of a mineral acid, or a substituted derivative thereof, selected from the group consisting of hydrochlorides, sulfates, nitrates, and phosphates.

6. The pharmaceutical composition according to claim 2, wherein the pharmaceutically acceptable salt is a salt of an organic acid, or a substituted derivative thereof, selected from the group consisting of acetates, propionates, succinates, benzoates, fumarates, tartrates, theophyllineacetates, salicylates, and phenolphthalinates.

7. The pharmaceutical composition according to claim 2, wherein the therapeutically effective amount of 6-(5-chloro-2-pyridyl)-5-[(4-methyl-1-piperazinyl)-carbonyloxy]-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine, or a pharmaceutically acceptable salt thereof, is from about 2.5 mg to about 15 mg.

8. The pharmaceutically composition according to claim 2, wherein the pharmaceutically acceptable carrier comprises a diluent.