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Enantioselective preparation of optically pure albuterol

Patent 5545745 Issued on August 13, 1996. Estimated Expiration Date: Icon_subject January 20, 2015. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Inventors

Assignee

Application

No. 376072 filed on 01/20/1995

US Classes:

560/42, Oxy in acid moiety564/304, Of benzene ring containing compounds564/356, Preparing directly by reduction, other than by reductive amination564/363, Beta hydroxy phenethylamines (i.e., hydroxy and the benzene ring are bonded directly to the same carbon of the chain which consists of two carbons; H of -OH may be replaced by a substituted or unsubstituted ammonium ion or a Group IA or IIA light metal)564/365Hydroxy or ether oxygen bonded directly to the aryl ring or ring system (H of -OH may be replaced by a substituted or unsubstituted ammonium ion or a Group IA or IIA light metal)

Examiners

Primary: Raymond, Richard L.

Attorney, Agent or Firm

Foreign Patent References

  • WO92/04314 WO. 03/13/1992

International Class

C07C 209/68

Abstract

The invention relates to a method for producing albuterol by the resolution of a mixture of enantiomers of methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-(phenylmethoxy)benzoate or ଱-[[(1,1-dimethylethyl)amino]methyl]-4-(phenylmethoxy)-1,3-benzenedi methanol using a chiral acid such as (+/-) di-toluoyltartaric acid or (+/-) di-benzoyltartaric acid.

Other References

  • Hartley et al. "Absolute Configuration of the Optical Isomers of Salbutamol" J. Med. Chem. 14, 895-896 (1971)
  • Hopkins, "Salbutamol" Drugs of the Future IV 629-633 (1979)
  • Floyd et al. "The Oxidation of Aetophenones to Arylglyoxals with Aqueous Hydrobromic Acid in Dimethyl Sulfoxide" J. Org. Chem. 50 5022-5027 (1985)
  • Collin et al. "Saligenin Analogs of Sympathomimetic Catecholamines" Chemistry Dept., Allen and Hansburys Ltd. (1970
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