Process for preparing a single enantiomer of a lactam using lactamase

Patent 5284769 Issued on February 8, 1994. Estimated Expiration Date:

May 20, 2013. 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.

Abstract Claims Description Full Text

Inventors

Assignee

Chiros Ltd.

Application

No. 063392 filed on 05/20/1993

US Classes:

435/280Resolution of optical isomers or purification of organic compounds or composition containing same

Examiners

Primary: Naff, David M.
Assistant: Meller, Michael V.

Attorney, Agent or Firm

Foley & Lardner

International Classes

C07C 007/00
C12N 009/78

Foreign Application Priority Data

1989-10-16 GB

Abstract

Lactams of 1-amino-3-carboxylic acid cyclic compounds are produced in enantiomeric form, together with an enantiomer of the corresponding ring-opened amino-acid or ester, by reaction of the racemic lactam with a novel lactamase. The products are useful in the synthesis of chiral carbocyclic nucleotides.

Other References

Morrison et al., Organic Chemistry, 5th ed., p. 136, 1987
CA 112:217364n, IK Bal et al., "Synthesis of the two Enantiomers of the Carbocyclic Analog of Nicotinamide Vibose and Analysis of their Biological Properties", Eur. J. Med. Chem., 1989, 24(4), 415-420
Caamano et al., Heterocycles, "An approach to the enantio selectur Synthesis of 2-Azabicycolo [2.2.1]Hept-5-en-zone," vol. 27, No. 12, 2839-2841, 1988
Evans et al., J. Chem. Soc. Perkin Trans. 1:656-657, 1991
Chemical Abstracts, vol. 93, No. 3, Jul. 21, 1980, p. 738, abstracts No. 26739t, Columbus, Ohio; R. D. Allan et al.: "Synthesis of analogs of GABA, III. All four stereoisomers of 3-aminocyclopentanecaroxylic acid and a stereochemical correlation with amidinomycin", Aust. J. Chem., 1979, 31(11), 2517-21
Chemical Abstracts, vol. 107, No. 5, Aug. 3, 1987, p. 648 abstract No. 39244k, Columbus, Ohio; R. D. Allen et al.: "Gamma-aminobutyric acid synthesis of analogs of GABA, XV.", and Chemical Abstracts, vol. 107, Chemicals Substances Index, part 2, 1987, pp. 2891CS, & Australian Journal of Chemistry, 1986, 39(6), 855-864
Chemical Abstracts, vol. 91, No. 25, Dec. 17, 1979, p. 25, abstract No. 204205j, Columbus, Ohio; G. A. R. Johnston et al.: "Stereospecific actions of GABA analogs", and ADV Pharmacol Ther., Proc. Int. Congr. Pharmacol, 7th 1978 (Pub. 1979) 2, 11-18
Journal of Organic Chemistry, vol. 43, No. 13, Jun. 9, 1978, pp. 2311-2320, American Chemical Society, Washington, D.C., S. Daluge et al.: "Synthesis of carbocyclic aminucleosides