2 years ago

Medicinal Chemistry Course

Medicinal Chemistry Course

N-alkylated omeprazole

N-alkylated omeprazole enantiomersare prone to stereomutate at sulfurOCH 3CCH 3COCH 3CH 3H 3SONNNR:H+HNH 3SO+NNR:OCH 3OCH 3C H 3OCH 3CH 3+NSOHN N ROCH 3Lindberg / von Ungeachiral sulphenic acid

Isomers of omeprazole- after 1990• Gram quantities prepared (and subsequently Kg´s)• Enough quantities to identify possible differences inpharmacokinetic and metabolic profile• Alkaline salts crystalline (as opposed to neutral form)• Salts stable against racemisation• A clear pharmacokinetic difference identified in rats• Opportunity to go quickly to human Phase ILindberg / von Unge

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