Optically active compounds

Details Optically active compounds Optically active compounds

2005-02-01

2005-02-01

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C544S258000

Reexamination Certificate

active

06849628

ABSTRACT:
The present invention relates to the preparation of substantially pure diastereoisomers of derivatives of tetrahydrofolate and the use of such diastereoisomers. More particularly the present invention provides a process for the preparation of a desired substantially pure (6R or 6S) diastereoisomer of a derivative of tetrahydrofolic acid or salt or ester. The process comprises the steps of: attaching a chiral auxiliary group at either N-5 or N-10 of a mixture of 6R and 6S diastereoisomers of tetrahydrofolic acid, separating the new diastereoisomers, recovering the desired new diastereoisomer (6R or 6S) corresponding to the desired (6R or 6S) diastereoisomer, and converting the substantially pure new diastereoisomer recovered into the corresponding diastereoisomer.

REFERENCES:
patent: 4959472 (1990-09-01), Wood et al.
patent: 5010194 (1991-04-01), Mueller
patent: 5134235 (1992-07-01), Mueller et al.
patent: 5347005 (1994-09-01), Mueller et al.
patent: WO 8808844 (1988-11-01), None
Rees et al., “Asymmetric Reduction of Dihydrofolate Using Dihydrofolate Reductase and Chiral Boron-Containing Compounds,”Tetrahedron, vol. 42, No. 1, pp. 117-136, (1986).
Fontecilla-Camps et al., “Absolute Configuration of Biological Tetrahydrofolates. A Crystallographic Determination.”Journal of the American Chemical Society, vol. 101, pp. 6114-6115 (Sep. 1979).
Temple et al., “Reversal of Methotrexate Toxicity in Mice by a Calcium Salt of Citrovorum Factor and Related Compounds,”Cancer Treatment Reports, vol. 65, No. 11-12, pp. 117-119 (Nov./Dec. 1981).
Chello, et al., “Further Studies of Stereospecificity at Carbon 6 for Membrane Transport of Tetrahydrofolates, Biochemical Pharmacology”, vol. 31, No. 8, pp. 1527-1530, 1981.
Kaufman, et al., “Chromatographic Separation of the Diastereoisomers of d 1.L-5, 10-Methylenetetrahydrofolate”,The Journal of Biological Chemistry, vol. 238, No. 4, Apr. 1963, pp. 1498-1500.
Blair, John A., “Chemistry and Biology for Pteridines, Pteridines and Folic Acid Derivatives”,Proceedings of the Seventh International Symposium on Pteridines and Folic Acid Derivatives Chemical, Biological and Clinical Aspects, St. Andres, Scotland, Sep. 21-24, 1982, p. 533.
Sirontnak, et al., “Stereospecificity at Carbon 6 o fFormyltetrahydrofolate As A Competitive Inhibitor of Transport and Cytotoxicity of Methotrexate in Vitro”,Biochemical Pharmacology, vol. 28, pp. 2993-2997, 1979.
Straw, James A. et al., “Differences in the Pharmacokinetics of the Disastereoisomers of Citrovorum Factor in Dogs”,Cancer Research 41, 3963-3939, Oct. 1981 and pp. 3936-3939, 3114-3119, Cancer Res. vol. 44 (1984).
J.C.S. Chem. Comm., 1974, pp. 175-176.
Machover, David, et al., “Treatment of Advanced Colorectal and Gastric Adenocarcinomas with 5-Fluorouracil and High-Dose Folinic Acid”,Journal of Clinical Oncology, vol. 4, No. 5, pp. 685-696 (May), 1986.
Feeny, J.,Biochemistry, vol. 20, p. 1837 (1981).
van Tamelen, et al., “Absolute Configuration of Biological Tetrahydrofolates, A Crystallorgraphic Determination”,Journal of American Chemical Society/101:20/Sep. 26, 1979, pp. 6114-6115.
Kalbermatten, R., 266, “Uber Pterinchemie”, Helvetica Chimica Acta, vol. 64, Fasc. 8 (1981), Nr. 266, pp. 2627-2635.
Blakely, R.L. et al., “Folates and Pterines”, vol. 1,Wiley Interscience, (New York 1984).
Moran, R.G. Moran et al., “A simple Procedure for the Synthesis of High Specific Activity Triated (6S)-5-Formyltetrahydrofolate”,Analytical Biochemistry, 122.70-78 (1982), p. 70-7.
Louslich, et al.,Journal Am. Chem. Soc., vol. 74, p. 4215-6 (1952).
Merck Index, 10thEd. (1983), entry 4111.
Rees et al.,J. Chem Soc Chem. Comm.,1987, p. 470-2.

Affiliated with

Also associated with

Rating

Optically active compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Optically active compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Optically active compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3478380