Design and Synthesis of N-heterocyclic Building Blocks for Pharmaceutical R&D. Feb 2016
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1 Design and Synthesis of N-heterocyclic Building Blocks for Pharmaceutical R&D Feb 2016
2 Who we are Liverpool ChiroChem (LCC) supplies chiral building blocks for pharmaceutical R&D. LCC also develop synthetic routes for complex intermediates and API. Established in Liverpool, U.K., June Currently based within the Department of Chemistry, University of Liverpool. Core technology: LCC s methods give access to a wide range of chiral building blocks in excellent enantiomeric purity. Our initial focus is on the production and supply of chiral piperidines and other sp 3 - rich nitrogen heterocycles, which are of great importance to drug discovery and development. Core strengths: Unique products; excellent chemical and enantiomeric purity. Expert service; specialist experience in method development and tech transfer.
3 Management Team Dr Jianjun Wu, CEO and Director Industrial Chemist and Entrepreneur. Founder of Shanghai Boc Chemical. Prof Jianliang Xiao, Director Professor of Chemistry at the University of Liverpool. Previously worked with Prof. Noyori (winner of the Nobel Prize in chiral chemistry). Dr Paul Colbon, COO and Director Industrial Chemist. Previously worked with Redx Pharma and AstraZeneca. Mr Bernard Ross, Non-exec Director CEO and Founder of Sky Medical Technology. Dr Jiwu Ruan, CSO and Director Industrial Chemist. Previously worked with Dr Reddys, Cambridge. Dr David Lathbury, Non-exec Chairman Industrial Chemist. Former director of AstraZeneca and AMRI.
4 Our expertise The founding team consists of chemists with academic and industrial experience that have developed state-of-the-art synthetic methods in asymmetric hydrogenation / transfer hydrogenation and palladium chemistry. The team is also experienced in process development and tech transfer. Asymmetric Hydrogenation /Transfer Hydrogenation (AH /ATH) Offering access to a wide variety of chiral products or APIs J. Am. Chem. Soc. 2008,130, J. Am. Chem. Soc. 2008, 130, J. Am. Chem. Soc. 2009, 131, J. Am. Chem. Soc. 2014, 136, Angew. Chem. Int. Ed. 2006, 45, Angew. Chem. Int. Ed. 2009, 48, Angew. Chem. Int. Ed. 2010, 49, Angew. Chem. Int. Ed. 2011, 123, Angew. Chem. Int. Ed. 2013, 52, 1668.
5 Our expertise Pd-Catalysed Coupling Reactions powerful strategy for construction of new C C and C X bonds, widely applied in APIs synthesis Acc. Chem. Res. 2011, 44, 614. J. Am. Chem. Soc. 2005, 127, 751. J. Am. Chem. Soc. 2008, 130, J. Am. Chem. Soc. 2008, 130, J. Am. Chem. Soc. 2010, 132, Angew. Chem. Int. Ed. 2006, 45, 4152.
6 Our products Production of chiral nitrogen heterocycles, that can be used as building blocks, fragments or screening compounds. Examples: Specific example of our building blocks can be browsed on our website under the catalogue tab.
7 4-substituted piperidines: Our products examples of current stock
8 Our products examples of current stock 3-substituted piperidines (provided as single enantiomers or racemic mixtures):
9 Our products examples of current stock 2-substituted piperidines (provided as single enantiomers or racemic mixtures):
10 Our products in the pipeline di-substituted piperidines: 2 and 3-substituted pyrrolidines: Trifunctionalised Piperidines: N-substituted piperidines:
11 Product Design Building Block Design LCC s heterocyclic building blocks are designed in partnership with MedChemica and Dr Neil Berry from the department of chemistry, University of Liverpool: Heterocyclic Synthesis - LCC s products are synthesised by our teams of expert chemists in the UK and China. Our wealth of experience in asymmetric synthesis and heterocyclic chemistry allows for efficient synthesis of novel molecules based upon our heterocyclic cores. Library Philosophy - Our sp 3 -rich heterocylcic cores ensure the molecules we produce occupy 3D space and have desirable pharmacokinetic properties. We design low molecular weight compounds with a wide range of functional groups and synthetic handles, so that hit fragments can be easily elaborated and optimised.
12 Focussed Library Design CNS LCC s synthetic technologies allow the production of novel, heterocyclic based small molecules. Our patented technology provides access to chiral piperidines. Upon analysis of the FDA approved drugs, we noticed that piperidines are the most frequently occurring heterocylce. In addition, piperidines are also the most prevalent heterocycle in clinically approved CNS (Central Nervous System) compounds. Therefore, we set out to apply our technology to the synthesis of a focussed library targeted at the CNS.
13 Focussed Library Design CNS Examination of the physicochemical/lipinski space of LCC compounds cf CNS approved drugs there is a high degree of similarity, i.e. low MW (<400), low logp (<5), #H bond donors (95% library <5), #H bond acceptors (<8).
14 Focussed Library Design CNS LCC produced an initial library set of ~11,000 molecules, which was designed in partnership with Medchemica, using MMPA and their grand rule database. The library was also designed in order to ensure a good range of functionality was incorporated. We then decided on the criteria upon which to optimise the library: Physicochemical and CNS penetration criteria were selected based on published literature (e.g. Ro3), experience (solubility > 1 milim) and targeting the CNS (MPO >4). MPO score devised by Pfizer: CNS penetration required Guidelines suggested - different to Lipinski s MPO score - probability of CNS penetration 74% CNS drugs have MPO score > 4 6 key physicochemical parameters (logp, logd, TPSA, MW, HBD, HBA, pka) drive library design
15 Focussed Library Design CNS Final set of criteria: o Calculated solubility > 1 millim o MPO score > 4 o AlogP < 3 o Molecular weight < 300 o #H bond donors < 3 o #H bond acceptors < 3
16 Focussed Library Design CNS Results: Out of the initial set of ~11,000 compounds, ~3,000 (27%) successfully met all of the criteria. MW Solubility MPO logp (mm) Average SD
17 Focussed Library Design CNS Results continued: A library of ~3000 small, fragment like, highly soluble, CNS penetrant compounds has been designed.
18 Focussed Library Design CNS Results continued: As can be seen below, the ~3000 compounds sit in a favourable area of MPO/logP/Solubility space all compounds have MPO score >4 (green).
19 Focussed Library Design CNS Results continued: In terms of shape, the 3000 compound library show a similar distribution in shape to currently approved CNS compounds. Concentrated near the rod-disc axis but with considerable 3D character (towards sphere point).
20 Our services chemistry capabilities 4 Highly experienced PhD chemists in all aspects of asymmetric hydrogenation, Pd-coupling and method development. 10 production chemists, 2 analysts and 1 procurement specialist. Carousel reactors and parallel hydrogenator. Process development and scale-up laboratory with 50L reactor and 20L rotary evaporator. 250mL, 1L and 5L Autoclaves for hydrogenation up to 50 barr. NMR, HPLC and GC analysis and quality control. Synthesis in the range of mg s to Kg s.
21 Website: Office Phone: +44 (0)
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