General provisions

Correspond to the earlier course 3FK023 Drug Synthesis.

Entry requirements

Attendance of all earlier courses within the pharmacy programme and of which 60 credits from term 1-2 should be passed. For single subject course 60 credits of which 45 credits is in pharmaceutical chemistry or equivalent is required.

 

Learning outcomes

On completion of the course the students should be able to:

• conduct laboratory work in accordance with safety requirements and document laboratory work and observations
• plan and carry out drug syntheses guided by the organic-chemical literature as well as explain orally and in writing the procedures, results and theory
• relate the acid / base strength and reactivity and stability of reactive intermediates to the structure
• describe organic chemical reactions and explain their associated reaction mechanisms and apply this to drug molecules. select and justify appropriate reagents for selective reactions of multifunctional molecules in the (drug) syntheses
• perform retrosynthetic analysis of (drug) molecules and propose multi-step syntheses for their preparation
• explain some modern synthesis methods and strategies relevant to drug discovery
• describe electron distribution/bondings in organic molecules by means of theoretical models built on inductive effects and resonance effects or molecular orbital models.

Content

The course focuses on organic synthesis strategy and synthesis methodology, mainly within the pharmaceutical field and of organic-chemical reaction mechanisms. Among the reaction types and associated mechanisms discussed are substitutions, eliminations, addition to alkenes, electrophilic and nucleophilic aromatic substitution, carbonyl reactions, reactions of carboxylic acid derivatives, oxidation, reduction, carbocation rearrangements, sigmatropic rearrangements, organometallic chemistry, enol and enolate chemistry and radical reactions. The organic chemical literature is illuminated and new synthetic methods and strategies of relevance to drug development are discussed, as well as SAR investigation, parallel synthesis and sustainable development. Also discussed concepts such as inductive effect, resonance, resonance effect, solvation and steric effects associated with molecules acid strength, base strength, reactivity and reactive intermediates stability. Selectivity in organic synthesis as well as simple protection group strategies are discussed. Furthermore, spectroscopic methods are treated theoretically and experimental (IR, MS and NMR). The laboratory part comprises organic synthesis of pharmaceutical substances and drug-like compounds and identification of organic compounds by means of different spectroscopic methods. Laboratory exercises are presented both orally and in writing.

Instruction

The teaching is given as lectures, group exercises, seminars, demonstrations and laboratory sessions. The laboratory sessions are presented orally and in writing.

Compulsory parts of the course: Compulsory parts of the course: Course introduction and all parts in connection with laboratory sessions. Laboratory work may be held in the evenings Laboratory sessions may be held in the evenings.

Assessment

To pass the whole course a passed laboratory and a passed examination) are required as well as attendance at all compulsory parts of the course. The laboratory sessions are examined orally and in writing. A chance to finalise a failed laboratory course can be given only at the next course occasion and only in case of a vacancy. Each student has the right to in all six examinations i.e. one examination and five re-examinations. Participation in an examination is counted as an examination. Submission of so called blank exam is counted as an examination. Submission of a so called blank exam is counted as one examination attempt.