Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-05-25
1999-08-10
Fonda, Kathleen K.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 41, 536 187, 536 53, 536127, 536128, 514 25, 424520, C07H 1500, A61K 3170
Patent
active
059360763
ABSTRACT:
The present invention relates to the novel .alpha.-galactosylceramide represented by the formula (A): ##STR1## wherein R represents ##STR2## where R.sub.2 represents H or OH and X denotes an integer of 0-26, or R represents --(CH.sub.2).sub.7 CH.dbd.CH(CH.sub.2).sub.7 CH.sub.3 and R.sub.1 represents any one of the substituents defined by the following (a)-(e):
REFERENCES:
patent: 4598051 (1986-07-01), Papahadjopoulos et al.
patent: 4728641 (1988-03-01), Tubaro et al.
patent: 4806466 (1989-02-01), Paphadjopoulos et al.
patent: 4816450 (1989-03-01), Bell et al.
patent: 4831021 (1989-05-01), Tubaro et al.
patent: 4859769 (1989-08-01), Karlsson et al.
patent: 4937232 (1990-06-01), Bell et al.
patent: 4952683 (1990-08-01), Tschannen
patent: 5026557 (1991-06-01), Estis et al.
patent: 5028715 (1991-07-01), Lyle
patent: 5041441 (1991-08-01), Rodin et al.
patent: 5073543 (1991-12-01), Marshall
patent: 5210073 (1993-05-01), Yodoi
patent: 5567684 (1996-10-01), Ladish
English translation of JP Application 93562/1989.
English translation of claims of Japanese Patent 2588729, 1996.
Zubay "Biochemistry", Benjamin/Cummings Publishing Co., Inc., 1983, p.527.
Sweeley, C. C. "Sphingolipids" p. 327-361, New Comprehensive Biochemistry--Biochemistry of Lipids, Lipoproteins and Membranes vol. 20, Elsevier 1991.
Sweeley, C. C. "Chemistry of Mammalian Glycolipids" p. 459-541 in The Glycoconjugates-vol. 1--Mammalian Glycoproteins edited Martin Horowitz 1977.
Mecher, B. A. et al. Glycosphingolipids . . . p. 236-250, Methods of Enzymology vol. L. Complex Carbohydrates Part C edited by Victor Ginsburg 1978 Academic Press.
Stults, C. L. M. et al. Glycosphingolipi pp. 167-214 in Methods of Enzymology vol. 179 Complex Carbohydrates Part F edited by Victor Ginsburg 1989, Academic Press.
Hakomori, Sen-itiroh "Chemistry of Glycosphingolipids" p. 1-165 in Handbook of Lipid Research vol. B. Sphingolipid Biochemistry ed. Donald J. Hanahan 1983.
Makita, A. Glycosphingolipids p. 1-99 in New Comprehensive Biochemistry vol. 10 ed. H. Wiegandt 1985.
Yu, R. K. et al. "Structure and Localization of Gangliosides" p. 1-42 in Neurobiology of Glycoconjugates ed. Richard U. Margolis (1989).
Nishizuka Y. Science 233, 305-312 (1986).
Kaibuchi K. et al. J. Biol. Chem. 260, 1366-1369 (1985).
Crabtree, G. R. Science, 243, 355-361 (1989).
Wepsic, T. H. et al. Immunopharmacol. Immunotoxicol. 11, 81-99 (1989).
R. J. Robb, The Journal of Immunology vol. 136, 971-976 (1986).
E. G. Bremer, The Journal of Biological Chemistry 261, 2434-2440 (1986).
Higuchi, R., et al. "Structure and Biological Activity of Ganglioside Molecular Species." Liebigs Annalen der Chemie, vol. 1993, No. 4, Apr. 1993, pp. 359-366.
Sugiyama, S., et al. "Biologically Active Glycosides . . . " Leibigs Annalen der Chemie; 1991, No. 4,pp. 349-356; (Apr. 4, 1991).
Schmidt, R.R., et al. Synthesis of D-ribo-and L-lyxo-Phytosphingosi Carbohydrate Research; vol. 174, (1988) pp. 169-179.
Koike, et al. Carbohydrate Research, vol. 162, No. 2, pp. 237-246, May 1, 1987.
Costello, et al. ACS Symposium Series: Gel Surface Glycolycide, vol. 128, pp. 35-54, 1980.
Higuchi, R. et al. "Structures of three New Cerebrosides . . . " Liebigs Ann Chem., 1990, 659-663.
Higuchi, R., et al "Isolation and Characterization . . . " Liebigs. Ann. Chem. 1990, 51-55.
Shiio, T. Jpn J. Cancer Chemother. 15(3) Mar. 1988, pp. 481-485.
Taguchi, T. Jpn. J. Cancer Chemother. 12(2) Feb. 1985, pp. 366-378.
Tanikawa, S. et al. Blood vol. 76, No. 3, Aug. 1, 1990, pp. 445-449.
Okano, A. et al. Transplantation, vol. 47, No. 4, p. 738-740 Apr. 1989.
Komori, T. et al. Mass Spectrometry Rev. 1985, 4, 255-293.
Kalechman, Y., et al. The Journal of Immunology. vol. 145, 1512-1517, Sep. 1, 1990.
Isobe, R., et al. "Biomedical and Environmental Mass Spectrometry" vol. 13, 585-594 (1986).
Tsunematsu, H. et al. Biochemical and Biophysical Research Communications, vol. 146, No. 2, 907-911 (1987).
Kodo, H. et. al. The Lancet. Jul. 2, 1988, pp. 38-39.
Blazar, B., et. al. Blood, vol. 74, No. 6, Nov. 1, 1989, pp. 2264-2269.
Tamura, M. et al. Transplantation vol. 51, No. 6, p. 1166-1170 Jun. 1991.
Atkinson, K. et al. Blood, vol. 77, No. 6, Mar. 15, 1991, pp. 1376-1382.
Teshima, H. Exp. Hematol. vol. 17, 1989, pp. 853-858.
Souza, L. M., et al, Science, vol. 232, pp. 61-65 Apr. 4, 1986.
Sheridan, W.P., et al. The Lancet, Oct. 14, 1989, pp. 891-895.
Brandt, S.J. The New England Journal of Medicine, vol. 318, Apr. 7, 1988, pp. 869-876.
Nienhuis, A. W. The Journal of Clinical Investigation. vol. 8, Aug. 1987, pp. 573-577.
Monroy, R.L. Blood. vol. 70, No. 5, Nov. 1987, pp. 1696-1699.
Ende, N. "Life Sciences" vol. 51, pp. 1249-1253, 1992.
Motoki, K. "Radioprotective Effects . . . " Bioorganic and Medicinal Chemistry Letters, vol. 5, No. 22, pp. 2413-2416, 1995.
Hall, Eric. J. "Radiobiology for the Radiologist" Second Ed., Ch. 1, 9 and 11, 1978, Harper and Row--Philadelphia.
Carroll, F.I., et al. J. Med. Chem., 1990, 33: 2501-2508.
Sato, K. et al. High-Performance Tandem Anal. Chem. 1987, 59, 1652-1659.
Y. Kawano et al. "Isolation and Structure of six . . . " Liebigs Annalen Der Chemie, vol. 1.
R. Higuchi et al. Structures of Three New. . . and Pharmaceutical Bulletin, vol. 39. No. 6, Jun. 1991.
K. Munesada, et al. Chem. Soc. Perkin Trans. 1991 p. 189-194.
M. Honda, Chem. Pharm. Bull 39(6) 1385-1391, 1991.
S. Hirsch et al. "New Glycosphingolipids . . . " Tetrahedron, vol. 45. No. 12, Dec. 1989, p. 3898.
Uchida, et al; J. Biochem. 87:1843-1849 (1980).
Yates, et al; Chemical Abstracts 93:112178r (1980).
Dyatlovitskaya, et al; Biokhimiya 49(3):432-436 (1984).
Singh, et al; Molecular & Biochemical Parasitology 26:99-112 (1987).
Inokuchi, et al; Cancer Letters 38:23-30 (1987).
Radin, et al; Biochemical Pharmacology 37(15):2879-2886 (1988).
Hannun, et al; Science 243:500-507 (Jan. 1989).
Kalisiak, et al; Int. J. Cancer 49:837-845 (1991).
Wiegand, et al; Chemical Abstracts 114:122965m (1991).
Dillman, et al; Molecular Biotherapy 4:117-121 (Sep. 1992).
Akimoto Koji
Higa Tatsuo
Koezuka Yasuhiko
Morita Masahiro
Natori Takenori
Fonda Kathleen K.
Kirin Beer Kabushiki Kaisha
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