Piperidine is an azacycloalkane that is cyclohexane in which one of the carbons is replaced by a nitrogen. Although piperidine is a common organic compound, it is an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.
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Morpholine contains secondary amine groups and has all the typical reactive characteristics of secondary amine groups. It can react with inorganic acids to form salts, and react with organic acids to form salts or amides, which can be subjected to alkylation reaction, and can also be reacted with ethylene oxide, ketone or Willgerodt reaction. Morpholine is a six-membered ring containing oxygen and nitrogen, and its alkalinity is much lower than that of its parent piperidine. The marketed morpholine drugs are mainly distributed in the fields of tumors, cardiovascular and cerebrovascular diseases, respiratory system diseases, digestive system diseases, infectious diseases and mental disorders.
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With four imidazopyridine-containing drugs and one pyrazolopyridine-containing drug on the market, bicyclic pyridines containing ring-junction nitrogen are privileged structures in medicinal chemistry. With two nitrogen atoms with potential to serve as hydrogen bond acceptors, imidazopyridines and pyrazolopyridines may boost binding to target proteins and elevate potency. In addition, these structures have found utility in FBDD, covalent inhibitors, reducing metabolic liabilities, and creating novel chemical space and intellectual properties. With many of the advanced intermediates now commercially available, they will find more and more applications in drug discovery.
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