Es wurde 1 Technologieangebote gefunden

Stereoselective Synthesis of cis-4-methylsphingosine and derivatives thereof


24.06.2011
| Ref.Nr. 10127
Life Science › Pharma&Biotech

Background
Sphingosine-1-phosphate is a bioactive lipid signaling molecule and an agonistic ligand of five specific G protein coupled receptors named S1P1-5.These receptors play a crucial role in the cardiovascular and immune system and in angiogenesis. The known compound FTY720 (Fingolimod) is a sphingosine analogue with immunosuppressive effects and was recently approved for treatment of multiple sclerosis in the United States and Russia.The synthetic sphingosine analogue Cis-4-methylsphingosine was firstly synthesized by R. R. Schmidt and coworkers in 1993 in nine steps.Similar to FTY720 this compound is phosphorylated in biological systems and inhibits the activity of different S1P-receptors, however the spectrum of receptors influenced by Cis-4-methylsphingosine is slightly different to that influenced by FTY720. Cis-4-methylsphingosine induces apoptosis of neuroblastoma cells.

Technology
We offer a rapid and simple method for the stereoselective synthesis of cis-4-methylsphingosine and derivatives thereof in only two steps. The novel synthesis is characterized by using easily accessible starting material, and an overall yield of nearly 30% which is almost 100-fold compared to the synthesis known in the art. Since Cis-4-methylsphingosine also influences S1P-receptors like FTY70, however with a slight different spectrum, this compound might have similar effects or might support or supplement the activity of FTY720. Thereby Cis-4-methysphingosine has a great potential for pharmaceutical application.   

IP Rights
EP patent application was filed in May 2011
 
Patent Owner
Humboldt-Universität zu Berlin

 

Application Area:
Preparation of cis-4-methylsphingosine
Development Stage: Proof of concept
Weitere Kategorien: Life Science, Pharma & Biotech
Bild des Benutzers Dr. Bettina Büttner
Licensing Manager: Dr. Bettina Büttner
T +49 30 2125 4835
F +49 30 2125 4822
Suitable Industry: Chemical, biotechnology and pharmaceutical industry
Benefits:
  • Reliable, easy and rapid method for the preparation of cis-4-methylsphingosine
  • Only two steps form starting material to cis-4-methylsphingosine
  •  Cost- and time-effective synthesi100-fold higher yield compared to state of the art synthesis