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Total Synthesis of Northebaine, Normorphine, Noroxymorphone Enantiomers and Derivatives via N-Nor Intermediates
Description of Technology:
A new synthetic process has been found in which nordihydrocodeinone, an early intermediate in the total synthesis of codeine and related compounds, is easily formed into a number of N-nor compounds. These N-nor compounds can be used as precursors in the formation of narcotics, narcotic antagonists, or narcotic agonist-antagonists.
The manufacture of drugs of this type, such as northebaine or normorphine, can now be done without the use of thebaine as starting material. The syntheses have fewer steps than previous methods, and also have high yields. In addition, very significant simplification of existing thebaine based processes for the manufacture of opiates can be expected.
Applications:
Potential new methodology for the synthesis of intermediates for drugs including naloxone, naltrexone, percodan and nalbuphine.
Market:
- More than a quarter of Americans suffer daily pain, a condition that costs the U.S. about $60 billion a year in lost productivity.
- Americans spent about $2.6 billion in over-the-counter pain medications and another nearly $14 billion on outpatient analgesics in 2004.
- Worldwide, nearly 300 million people are believed to suffer from chronic pain.
Inventors:
Kenner C. Rice et al. (NIDDK)
Patent Status:
DHHS Reference No. E-012-1986/1 --
- Australian Patent 642447 issued 15 Feb 1994
- Japanese Patent 2694156 issued 12 Sep 1997
- Canadian Patent 2067200 issued 30 Jun 1998
- European Patent 0496830 issued 31 Mar 1999 in Austria, Belguim, Switzerland, Germany, Denmark, Greece, Luxembourg, Spain, Belgium, Netherlands, Sweden, France, Italy and United Kingdom
DHHS Reference No. E-012-1986/2 --
- United States Patent 5,668,285 issued 16 Sep 1997
Licensing Status:
Available for licensing.
Portfolios:
Central Nervous System - Therapeutics, neurological, narcotics and analgesics
Central Nervous System - Research Materials, synthesis methods
For additional information, please contact:
Charlene A. Sydnor, Ph.D.
Office of Technology Transfer
National Institutes of Health
6011 Executive Boulevard, Suite 325
Rockville MD 20852
Phone: 301/435-4689
Fax: 301/402-0220
Email: sydnorc@mail.nih.gov
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