Integrated approach for environmentally benign C-C coupling reactions

Project Information

CC-Coupler

Grant agreement ID: 827627

DOI

10.3030/827627

Project closed

EC signature date 2 August 2018

Start date 1 September 2018

End date 31 January 2019

Funded under

• INDUSTRIAL LEADERSHIP - Innovation In SMEs

Total cost

€ 71 429,00

EU contribution

€ 50 000,00

Coordinated by

ORGANOCHEM KUTATASI ES TANACSADO KORLATOLT FELELOSSEGU TARSASAG
Hungary

Periodic Reporting for period 1 - CC-Coupler (Integrated approach for environmentally benign C-C coupling reactions)

Reporting period: 2018-09-01 to 2019-01-31

Summary of the context and overall objectives of the project

Pharmaceutical industry is continuously looking for new and more effective drug candidates, and at the same time cleaner and more environmentally friendly processes. One of the most important family of chemical reaction is the formation of carbon-carbon bond by Pd mediated C-C coupling. It is estimated, that more than 50% of new drug synthesis will include at least one C-C coupling reactions. However, there are several issues regarding this reaction related to high environmental impact, complicated processes due to air-sensitive catalyst, post-processing, solvent issues, and catalyst recovery.

Our company provides products and services for pharmaceutical companies, universities, research institutes and government agencies. Our mission is to become a global leader in the provision of medicinal chemistry and chemistry services to the pharmaceutical, biotech and associated industries. We have developed a new integrated approach for carrying out C-C coupling reactions in an environmental benign and cost-effective way. Our CC-Coupler method targets to overcome all the issues regarding the reaction. Our aim is to commercialise the CC-Coupler as an integrated technology, providing the air-stable, highly performant catalyst with an adequate flow-chemistry device and parameter set optimised for the clients’ needs.

Work performed from the beginning of the project to the end of the period covered by the report and main results achieved so far

In this Phase 1 project we examined the feasibility of our approach. Regarding the technical feasibility, we demonstrated the efficiency of our CC-Coupler approach on reactions, which are theoretically possible, but no examples are provided in the literature, resulting compounds are biologically active and potentially interested by pharmaceutical companies. We successfully synthetized 6 new compounds and optimised the reaction conditions for them. In addition, we continued the reactor development and obtained graphical user interface (GUI). Furthermore, we optimised the catalyst formulation and its filling to cartridges. We also validated our business assumptions. We performed a detailed market study, including questionnaire and interviews with potential customers. The main result of this study is that the most important reason for choosing a catalyst is its performance. Thus, we must provide large variety of examples to prove the performance of our C-C coupler approach, to promote our sales. We carried out a detailed risk assessment and updated our IPR strategy.
As a result of the actions, we updated our business plan and defined main points of a subsequent Phase 2 application: work packages, objectives, tasks, and resources were defined.

Progress beyond the state of the art and expected potential impact (including the socio-economic impact and the wider societal implications of the project so far)

Our CC coupler approach is superior to the state of the art solutions as we demonstrated in several examples:
1) The catalyst provides an excellent performance, and it is air-stable;
2) The flow reactor system tailored for the purpose of C-C coupling is unique;
3) The environmental factor of our process is considerably lower than literature examples.

According to our knowledge there is no other commercially available integrated approach for carrying out C-C coupling reactions in a flow reactor system at laboratory scale, only the catalysts themselves and sometimes columns filled with Pd catalysts are available on the market.

Application of our solution contributes to the reduction of environmental effects of chemical industry in general, particularly of pharmaceutical industry, since the proposed process is environmentally benign, and the environmental efficiency of our process (i.e. E-Factor) can be clearly identified. Furthermore, our process contributes to the development of new drug candidates and new chemical reactions to synthesize these new drug candidates. Finally, our process have impact on the challenge to reduce the dependency of Europe on rare earth metals (China, Russia, etc.), since in our methodology lower metal loading is applied and the recovery of metals in the flow reactor system is simple (e.g. by scavenger cartridges).

The success of the project will also impact our company by enhancing our profitability and growth.

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