Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1998-07-02
1999-11-09
Lambkin, Deborah C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
549 70, 549 71, 549 72, C07D51300, C07D33322, C07D33338
Patent
active
059817488
ABSTRACT:
The invention relates to methods of making compounds of the formula VII ##STR1## and their enantiomers, where Ar is a substituted or unsubstituted five- or six-membered aromatic group and B is either an amino acid linked through the amino portion to form an amide or a C.sub.1 -C.sub.6 alcohol linked through the alcohol portion to form an ester. These compounds are advantageously employed as intermediates to prepare optically pure compounds that are active GARFT inhibitors. In one method, a compound of the formula ##STR2## is reacted with a compound of the formula ##STR3## where X is a halogen.
REFERENCES:
patent: 4123550 (1978-10-01), Untch et al.
patent: 4684653 (1987-08-01), Taylor et al.
patent: 4686223 (1987-08-01), Cohnen et al.
patent: 4831037 (1989-05-01), Taylor et al.
patent: 4845216 (1989-07-01), Taylor et al.
patent: 4871743 (1989-10-01), Taylor et al.
patent: 4871746 (1989-10-01), Taylor et al.
patent: 4880812 (1989-11-01), Kelley
patent: 4882333 (1989-11-01), Shih et al.
patent: 4882334 (1989-11-01), Shih et al.
patent: 4883799 (1989-11-01), Taylor et al.
patent: 4889859 (1989-12-01), Taylor et al.
patent: 4895946 (1990-01-01), Taylor et al.
patent: 4920125 (1990-04-01), Taylor et al.
patent: 4921836 (1990-05-01), Bigham et al.
patent: 4927828 (1990-05-01), Taylor et al.
patent: 4971973 (1990-11-01), Bigham et al.
patent: 4973715 (1990-11-01), Roux et al.
patent: 4988813 (1991-01-01), Taylor et al.
patent: 5013738 (1991-05-01), Taylor et al.
patent: 5015656 (1991-05-01), Fernandez et al.
patent: 5026851 (1991-06-01), Taylor et al.
patent: 5034049 (1991-07-01), Kober et al.
patent: 5179123 (1993-01-01), Djuric et al.
patent: 5217974 (1993-06-01), Grindey et al.
patent: 5223503 (1993-06-01), Gossett et al.
patent: 5594139 (1997-01-01), Varney et al.
patent: 5608082 (1997-03-01), Varney et al.
patent: 5831100 (1998-11-01), Varney et al.
Moran, "Folate antimetabolites inhibitory to de novo purine synthesis," New Drugs, Concepts and Results in Cancer Chemotherapy, (Muggia ed.), Kluwer Academic Publishers, Boston (1992), 65-87.
Young et al., "An Antibody Probe to Determine the Native Species of Glycinamide Ribonucleotide Transformylase in Chicken Liver," Biochemistry, vol. 23, No. 17 (1984), 3979-3986.
Morrison, "Kinetics of the Reversible Inhibition of Enzyme-Catalysed Reactions by Tight-Binding Inhibitors," Biochem. Biophys. Acta, vol. 185 (1963), 269-286.
Totani et al., "Synthesis of a Novel 5-Deaza-5-thia Analogue of Tetrahydrofolic Acid . . . ," J. Chem. Soc. Perkin Trans. 1 (Apr. 1994), 833-836.
Mosmann, "Rapid Colorimetric Assay for Cellular Growth and Survival . . . ," J. Immunol. Methods, vol. 65 (1983), 55-63.
Sako et al., "New and Facile Synthesis of 5,6,7,8-Tetrahydro-5-deaza-5-thiapterins . . . ," Chem. Pharm. Bull., vol. 42, No. 4 (1994), 806-810.
Antony, "The Biological Chemistry of Folate Receptors," Blood--The Journal of the American Society of Hematology, vol. 79, No. 11 (1992), 2807-2820.
Pizzorno et al., "5,10-Dideazatetrahydrofolic Acid (DDATHF) Transport in CCRF-CEM and MA104 Cell Lines," The Journal of Biological Chemistry, vol. 268, No. 2 (1993), 1017-1023.
Alati et al., "Evaluation of the Mechanism(s) of Inhibition of the Toxicity, But Not the Antitumor Activity of Lometrexol . . . ," Proceedings of the Am. Assoc. for Cancer Res., Abstract 2432, vol. 33 (1992), 407.
Shih et al., "Synthesis and Biological Activity of Acyclic Analogues of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid," J. Med. Chem., vol. 35 (1992), 1109-1116.
Nemec et al., "The Synthesis of 4-Substituted 2-Thiophenecarboxylic Acids," Collection Czechoslov. Chem. Commun., vol. 39 (1974), 3527-3531.
Taylor et al., "Convergent and Efficient Palladium-Effected Synthesis of . . . (DDATHF)," J. Org. Chem., vol. 54, No. 15 (1989), 3618-3624.
Habeck et al., "A Novel Class of Monoglutamated Antifolates Exhibits Tight-binding Inhibition of Human Glycinamide Ribonucleotide Formyltransferase and Potent Activity Against Solid Tumors," Cancer Research, vol. 54 (Feb. 15, 1994), 1021-1026.
Henrie II et al., "Preparation of 2-Amino-4(3H)-oxopyrimido[5,4-b] [1,4]-thiazines . . . ," J. Med. Chem., vol. 26, No. 4 (1993), 559-563.
Okafar, "Studies in the Heterocyclic Series XVIII . . . ," J. Heterocyclic Chem., vol. 17 (1980), 1587-1592.
Alley et al., "Feasibility of Drug Screening with Panels of Human Tumor Cell Lines Using Microculture Tetrazolium Assay," Cancer Res., vol. 48 (1988), 589-601.
Cleland, "The Kinetics of Enzyme-Catalyzed Reactions with Two or More Substrates or Products," Biochem. Biophys. Acta, vol. 67 (1963), 173-187.
Casarrubio et al., "On the Syntheses of Thiophene Analogs of Practolol and `Reversed` Practolol," J. Heterocyclic Chem., vol. 20 (Nov.-Dec. 1983), 1557-1560.
Kisliuk et al., Chemical Abstracts, vol. 113, No. 9, Abstract No. 70792k (1990).
Sako et al., "First Synthesis of 5,6,7,8-Tetrahydro-8-deaza-thiafolic Acid," Chem. Pharm. Bull., vol. 40, No. 1 (1992), 49-52.
Taylor et al., "Studies on the Molybdenum Cofactor. Determination of the Structure and Absolute Configuration of Form A," J. Am. Chem. Soc., vol. 111, No. 19 (1989), 7664-7665.
Palmer Cynthia L.
Romines William H.
Varney Michael D.
Agouron Pharmaceuticals , Inc.
Lambkin Deborah C.
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