Orange Crowned Warbler

by | Dec 21, 2017 | Warblers

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Oxitropium bromide (trade names Oxivent, Tersigan) is an anticholinergic used as a bronchodilator for the treatment of asthma and chronic obstructive pulmonary disease.[1]

It was patented in 1966 and approved for medical use in 1983.[2]

Synthesis

The natural product, norscopolamine (1),[3] is converted by two alkylation reactions into oxitropium bromide. The first, with bromoethane, gives the N-ethyl intermediate (2), which is treated with bromomethane.[4] [5][6]

References

  1. ^ Restrepo RD (July 2007). "Use of inhaled anticholinergic agents in obstructive airway disease". Respiratory Care. 52 (7): 833–51. PMID 17594728.
  2. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 447. ISBN 9783527607495.
  3. ^ Ripperger, H (1995). "(S)-scopolamine and (S)-norscopolamine from Atropanthe sinensis". Planta Med. 61: 292–3. doi:10.1055/s-2006-958082. PMID 7617778.
  4. ^ Rolf Banholzer, Werner Schulz, Gerhard Walther, Helmut Wick, Karl Zeile, U.S. patent 3,472,861 (1969 to Boehringer Sohn Ingelheim).
  5. ^ Rolf Banholzer, Werner Schulz, & Karl Zeile, U.S. patent 3,538,102 (1970 to CH Boehringer Sohn AG and Co KG, Boehringer Ingelheim GmbH).
  6. ^ "Oxitropium bromide". Thieme. Retrieved 2024-07-01.
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