C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuro

Details C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuro C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuro

1994-09-30

1996-05-14

Chan, Nicky

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

549417, A61K 3135, C07D30914

Patent

active

055167926

ABSTRACT:
The present invention provides breast cancer chemopreventive arylamide analogues of retinoic acid, more particularly C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide and N-glycoside analogue of retinoyl .beta.-glucuronide that resist both .beta.-glucuronidase mediated enzymatic hydrolysis as well as acid catalyzed hydrolysis. Specifically, the drugs include 4-(retinamido)phenyl-C-glucuronide; 4-(retinamido)phenyl-C-glucoside; 4-(retinamido)benzyl-C-xyloside; 4-(retinamido)benzyl-C-glucoside; 4-(retinamido)benzyl-C-glucuronide; 4-(retinamido)phenyl-C-xyloside, 1-(B-D-glucopyranosyl) retinamide and 1-(D-glucopyranosyluronosly) retinamide. The invention also relates to a method for making such drugs.

REFERENCES:
patent: 5061723 (1991-10-01), Barua et al.
"N-Linked Analogs of Retinoid O-Glucuronides" by Robarge, et al., Bioorganic & Medical Chemistry Letters, vol. 4, No. 17, Aug. 1994, pp. 2117-2122.
"N-Linked Analogs of Retinoid O-Glucuronides" by Robarge, et al. (Abstract) Am. Chem. Society 25th Cent. Reg. Meeting, Oct. 4-6, 1993.
"Synthesis and Evaluation of N-Linked Glycoside Analogs of Retinoic Acid" by Robarge, et al., 27th Annual Mid-Atlantic. Sympos., Jul. 1994 (Abstract).
"Synthesis of N-Linked Glycoside Analogs of Retinoic Acid" by Robarge et al. Am. Chem. Soc., Aug. 21-25, 1994 (Abstract).
"N-and C-Glycoside Analogs of Retinoid O-Glucuronides and Their Breast Cancer Inhibitory Potential" by Panigot, et al., XIII Int. Symp. (Paris), Sep. 1994 (Abstract).
Biochemical Pharmacology, vol. 41, No. 10, issued 1991, Bhatnagar et al., "Growth Suppression of Human Breast Carcinoma Cells in Culture by N-(4-Hydroxyphenyl) Retinamide and its Glucuronide and Through Synergism With Glucarate, " pp. 1471-1477.
Journal of the National Cancer Institute Monographs, No. 12, issued 1992, Veronesi et al., "Chemoprevention of Breast Cancer With Retinoids," pp. 93-97.
Journal of Lipid Research, vol. 26, issued 1985, Barua et al., "Chemical Synthesis if All-Trans Retinoyl Betaglucuronide," pp. 1277-1282.

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