By Jie Jack Li, Douglas S. Johnson, Drago R. Sliskovic, Bruce D. Roth
Written via individuals of Pfizer worldwide learn and improvement for chemists coming into the pharmaceutical undefined, this paintings profiles the synthesis of fourteen consultant pharmaceutical items that allows you to reveal the multidisciplinary nature of the exercise. for every drug, they supply a old advent and the organic, pharmacological, pharmakinetic, and drug metabolism history ahead of detailing the drug's synthesis.
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Extra resources for Contemporary Drug Synthesis
Anti-inflammatory Cyclooxygenase-2Selective Inhibitors: Celecoxib and Rofecoxib 17 3 phenylpropargyl alcohol with 4-methylthiophenylmagnesium chloride followed by oxidation with m-CPBA afforded 2 in quantitative yield. CO (lOOatm), Rh4(C0)12 c EtSN, THF, H20, 1OOOC, 5 h o"s Me' "0 2 19 PhH, 8OoC, 19 h then rn-CPBA, 99% 2 Scheme 4. The rhuthenium-catalyzed and magnesium-mediated furanone formation. * Thus Friedel-Crafts acylation of thioanisole was performed employing the AICl&H$2OCl complex in o-dichlorobenzene (o-DCB) to furnish 4(methy1thio)acetophenone (10).
Phenylaminopyrimidine 5 was initially identified from a random screening as a PKC-a inhibitor with an ICso of approximately 1 pM. It did not inhibit Abl (an abnormal protein tyrosine kinase) and PDGFR (platelet-derived growth factor receptor, a kinase). Intensive SAR studies involving more than 300 analogs eventually led to imatinib mesylate (1). Significantly, the introduction of the “flag-methyl group” at the 6-position of the phenyl ring (highlighted in Figure 2) abolished the activity against PKC-a.
2 Synthesis of Esomeprazole The synthesis of esomeprazole (2) is illustrated below. 10 11 Pyridylmethyl chlonde 11 was obtained by direct chlorination of alcohol 10 using thionyl chloride3-' The hydroxymethyl-pyndine 10, in turn, was synthesized from 3 3 dimethylpyndine in 6 steps utilizing a Boekelheide reaction6 that transformed the 2methylpyridine-N-oxide to the corresponding h ydrox ymethyl-pyridine 10. 12 13 reflux, 2 h, 70% Methoxyphenylene diamine 12 was treated with potassium ethylxanthate to afford benzimidazole-thiol 13.