U.S. patents available from 1976 to present.
U.S. patent applications available from 2005 to present.

Process for the production of alpha-6-deoxytetracyclines

Patent 4997959 Issued on March 5, 1991. Estimated Expiration Date: Icon_subject April 13, 2009. 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.

Patent References

2984986

3200149

3444198

3489786

3549780

3639439

3703561

3907890

Process for producing ଱-6-deoxytetracyclines
Patent #: 3954862
Issued on: 05/04/1976
Inventor: Morris, Jr.

Rhodium containing catalyst and use thereof in preparation of 6-deoxy-5-oxytetracycline
Patent #: 3962131
Issued on: 06/08/1976
Inventor: Faubl ,   et al.

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Inventors

Assignee

Application

No. 337288 filed on 04/13/1989

US Classes:

552/206Processes

Examiners

Primary: Raymond, Richard L.
Assistant: Covington, Raymond

Attorney, Agent or Firm

Foreign Patent References

  • 2216268 FR. 08/13/1974
  • 1121642 GB. 07/13/1968
  • 1121643 GB. 07/13/1968
  • 1138601 GB. 01/13/1969
  • 1219763 GB. 01/13/1971
  • 2025403 GB. 01/13/1980

International Classes

C07C 103/19
C07C 237/00

Abstract

A process for the hydrogenation of a 6-methylenetetracycline in the production of alpha-6-deoxytetracycline, particularly the antibiotic doxycycline, in the presence of a transition metal complex of the formula MClx (PPh3)y wherein M is Cu, Co or Ni, x is 1 or 2 and y is 1-3, and a trace of rhodium either as the supported metal or as a rhodium salt, as a hydrogenation catalyst. The desired alpha-6-deoxytetracycline product is produced in high yields and stereospecificities. The process requires the use of substantially cheaper transition metal complexes and only traces of rhodium in the hydrogenation catalyst per mole of the 6-methylene tetracycline hydrogenated.

Other References

  • Vol. Pin et al., Russian Chemical Rev. 38, 273-289 (1969)
  • Augustine et al., Ann. N.Y. Sci., 148, 482-91 (1969)
  • Ruesch et al., Tetrahedron vol. 25, 805-11 (1969)
  • Wilkinson et al., J. Chem. Soc. 1711-32 (1966)
  • Knowles et al., Chem. Comm., 1445 (1968)
  • Horner et al., Angew. Chem. Internat. Edit. 7, 942 (1968)
  • Frey et al., Chem. Comm., 1069-70 (1969)
  • Manfredi, Milan, Italy, ACS 70
  • Grubbs et al., J. Am. Chem. 93, 3062 (1971)
  • Kagan et al., J. Am. Chem. Soc. 94, 6429 (1972)
  • Knowles et al., Chem. Comm. 10, (1972)
  • Harmon et al., Chem. Rev. 73, 21-52 (1973)
  • Theissen, J. Org. Chem. vol. 36, 752-757 (1971) (abstract)
  • Toniolo et al., Chim. Ind. Milan, 58(10), 732 (1976)
  • Fleet et al., Tetrahedron Letters No. 11, 975-8 (1979
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