5'-deoxy-cytidine derivatives

Details 5'-deoxy-cytidine derivatives 5'-deoxy-cytidine derivatives

2000-01-14

2000-09-05

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 2851, 536 2852, 514 49, C07H 1906, C07H 19067

Patent

active

061145203

ABSTRACT:
Novel 5'-deoxy-cytidine derivatives represented by the general formula (I) ##STR1## wherein R.sup.1 is a hydrogen atom or a group easily hydrolyzable under physiological conditions; R.sup.2 is a hydrogen atom, or --CO--OR.sup.4 group [wherein R.sup.4 is a saturated or unsaturated, straight or branched hydrocarbon group consisting of one to fifteen carbon atoms, or a group of the formula --(CH.sub.2).sub.n --Y (in which Y is cyclohexyl or phenyl; n is an integer from 0 to 4)]; R.sup.3 is a hydrogen atom, bromo, iodo, cyano, a C.sub.1-4 alkyl group [which may be substituted with halogen atom(s)], a vinyl or ethynyl group [which may be substituted with halogen atom(s), C.sub.1-4 alkyl, cycloalkyl, aralkyl, or aromatic ring which may have one or more hetero atom(s)], or an aralkyl group which may be substituted for use in medical therapy, especially tumor therapy.

REFERENCES:
patent: 4071680 (1978-01-01), Cook
patent: 4328229 (1982-05-01), Fuji et al.
patent: 4395406 (1983-07-01), Gacek et al.
patent: 4966891 (1990-10-01), Fuji et al.
patent: 5472949 (1995-12-01), Arasaki et al.
patent: 5476932 (1995-12-01), Brinkman et al.
patent: 5525603 (1996-06-01), Shirasaka et al.
patent: 5736531 (1998-04-01), Von Borstel et al.
Kim et al., "Stereospezifische Syntheses des Carcerostatikums 5'-Deoxy-5-fluor-uridine (5-DFUR) und Seiner 5'-Deuterierten Derivate," Helvetica Chim Acta, 65(5), 1523-1537 (1982).
Perman et al., "Synthesis of 1-(2-Deoxy-.beta.-D-erythro-pentofuranosyl)-5-ethynyl-1,2,3,4-tetrahydropy rimidine-2,4-dione (5'-Ethynyl-2'-deoxyurdines)," Tetrahedron Letters, (Issue No. 28), 2427-2430 (1976).
Farina et al., "Palladium-Catalyzed Approach to 5-Substituted Uracil and Uridine Derivatives," Synlett, 157-159 (Mar., 1991).
Naguib et al., "Structure-Activity Relationship of Ligands of Dihydrouracil Dehydrogenase from Mouse Liver," Biochemical Pharmacology, 38(9), 1471-1480 (1989).
Jones et al., "Synthesis of 5-Ethynylcytosine and 5-Ethynylcytidine," Tetrahedron Letters, (Issue No. 28), 2459-2460 (1977).
Nio et al., "A Comparative Study of the Antitumor Activities of 5'-Deoxy-5-fluorouridine and Its Prodrug Trimethoxybenzoyl-5'-deoxy-5-fluorocytidine (Ro09-1390) on Human Digestive Organ Cancer Xenograft Lines Transplanted into Nude Mice," Anti-Cancer Drugs, 3(4), 387-393 (1992).
Ishikawa et al., "Antitumor Activities of a Novel Fluoropyrimidine, N.sup.4 -Pentyloxycarbonyl-5'-deoxy-5-fluorocytidine (Capecitabine)," Biological and Pharmaceutical Bulletin, 21(7), 713-717 (Jul., 1998).
Scarano et al., "Enzymatic Deamination of 5'-Deoxycytidylic Acid and 5-Methyl-5'-deoxycytidylic Acid in a Developing Sea Urchin Embryo," Exptl. Cell Research, 18, 333-346 (1959); Chem. Abstr., 55(8), Abstr. No. 7681i, (Apr. 17, 1861); only Abstract supplied.
Talarico et al., "Enzymatic Deamination of 5'-Deoxycytidylic Acid in the Embryonic Chick Tissue," Bull. Soc. Ital. Sper., 36, 1056-1058 (1980); Chem. Abstr., 63(11), Abstr. No. 11730c (May 27, 1963); only Abstract supplied.
Theilheimer, Synthetic Methods of Organic Chemistry, vol. 7, S. Karger AG, Basel, Switzerland, 1953, only p. 16 supplied.
Krecmerova et al.(I), "Synthesis of 5-Phenylcytosine Nucleoside Derivatives," Collection of Czech. Chemical Communications, 61(4), 645-655 (1966).
Krecmerova et al.(II), "Preparation of 5-Benzyluracil and 5-Benzylcytosine Nucleosides as Potential Inhibitors of Uridine Phosphorylase," Collection of Czech. Chemical Communications, 61(4), 627-644 (1966).
Hrebabecky et al., "Reaction of Nucleosides with Thionyl Chloride; Preparation of the Deoxy Derivatives of Cytosine and Adenosine," Collection of Czech. Chemical Communications, 45(2), 599-605 (1980).

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