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Asymmetric Hydrogenation of PZQ-enamide

Published by MatTodd on 11 August 2010 - 10:25am

A possible solution to the large-scale preparation of enantiopure PZQ is the approach shown below, originally suggested by Craig Williams.
 

 
First step:

Catalyst screening for the Brønsted-catalysed Pictet-Spengler reaction to PZQ

Published by Michael Wolfle on 4 August 2010 - 3:23am

We started catalyst screenings for the asymmetric Pictet-Spengler reaction. So far, we have tested several achiral Brønsted-acidic catalysts to determine acid strength which is required to cyclize the open-chain praziquantel intermediate 1 to the tetrahydroisoquinoline heterocycle 2.
 
Scheme1
 
Catalysts:
 

Formulation possibilities

Published by ndt228 on 22 July 2010 - 10:59pm

 I came upon this reference:
http://www3.interscience.wiley.com/journal/123349682/abstract
which refers to masking of bitter taste of an API through formulation with a beta-cyclodextrin derivative.

Project Planning

Published by ndt228 on 4 July 2010 - 1:39pm

Based on past experience with "Chiral Switch" projects in a commercial environment, I have drafted the attached document as a summary of my understanding of the aims of the PZQ project in the context of what would be needed (technically) to get (R)-PZQ to market in the western world.  This does not examine manufacture per se, but rather the many necessary steps to obtain permission to market.  I am sure there are some which I may have missed, but the point is that there would (in my past experience) be far more going on than focussing as at present on "manufacture" and "cost of goo

PZQ Manufacturing Capacity

Published by MikeGretes on 12 June 2010 - 1:04am

Subject 

Request for Help

Let's think long-term: How best to scale up production of PZQ?

Catalyst Screening

Published by haynesp on 9 June 2010 - 10:18am

Project to determine if it is feasible to automate / accelerate the catalyst screening project through automated software systems. 
Currently the project is in requirements initiation. We are defining top level requirements of what an automated tool will look like.  Please feel free to contribute
Following link will be where requirements are documented. (This should support anonymous access).

Multistep synthesis of rac-PZQ (Ugi route)

Published by jcbradley on 1 June 2010 - 2:57am

A new patent application using a multistep reaction (Ugi reaction) for the synthesis of Praziquantel
 
Scheme1
 

25 May

New ELN for Pictet-Spengler Approach

Published by MatTodd

To host the raw data from the Pictet-Spengler approach to the enantioselective synthesis of PZQ Michael has started an Electronic Lab Notebook. We're using the open source Southampton Lab Blog interface for this, since we're collaborating with them on a couple of things related to this site.
 

Chiral HPLC method development PZQAmine at Syncom B.V.

Published by Jean-Paul Seerden on 24 May 2010 - 10:17pm

There is good news regarding the separation of the racemic praziquanamine with chiral HPLC.

  • Syncom B.V., The Netherlands, a CRO specialized in all aspects of organic synthesis, with a 20-year track record in resolution of chiral compounds, screened five different chiral HPLC columns, varied the eluent and used UV detection (220 and 260 nm) and a PDR-Chiral Advanced Laser Polarimeter.

 

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