Isometheptene isomer

US9403755B2 · kind B2 · utility

Assignee

• TONIX PHARMA HOLDINGS LIMITED (BERMUDA) · BM

Inventors

• Seth Lederman · New York, US
• Bruce Daugherty · South Orange, US
• Leland J. Gershell · New York, US
• Darryl Rideout · Del Mar, US
• Andrew M. Kawasaki · San Diego, US

Key dates

• Filing date: Jan 17, 2014
• Grant date: Aug 2, 2016
• Expiry date: Mar 18, 2034

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B2200/07
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The invention relates to a purified Isometheptene compound comprising the structure according to Formula (I),or a hydrochloride, or a pharmaceutically acceptable addition salt thereof. In particular, the disclosure relates to the synthesis, purification and characterization of an Isometheptene isomer mucate crystal 2, wherein the Isometheptene isomer 2 is stereochemically characterized as (R)-enantiomer, respectively. The Isometheptene (R)-enantiomer activity indicates a selective centrally acting selective ligand for Imidazoline subtype 1 (I1) receptor sites; and more specifically, the disclosure provides an antihypertensive composition for treatment of migraine and other neurovascular or neurogenic pain from abdominal distress. (R)-Isometheptene enantiomer or isomer 2 may be an anti-hypertensive agent with lower side effects than the racemate form. Therefore (R)-Isometheptene is believed to be effective against episodic tension-type headaches (ETTH). The (R)-Isometheptene enantiomer or isomer 2 is believed to effectively lower blood pressure, used alone or together with other headache ameliorating drugs. Methods of synthesis and treatment are described. Regarding (R)-Isomethepten…