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

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

1995-06-06

1997-09-02

Chan, Nicky

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30914

Patent

active

056633777

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 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; and 4-(retinamido)phenyl-C-xyloside.

REFERENCES:
patent: 4855463 (1989-08-01), Barma et al.
patent: 5061723 (1991-10-01), Barua et al.
Abstract: "Cancer Chemopreventive Retinoid Metabolites: C-Glucuronide Analogues of 4-Hydroxyphenylretinamide-O-glucuronide" by Panigot et al., presented at the Fourth Chemical Congress of North America, in New York, New York on Aug. 25-30, 1991.
Abstract: "Preparation of C-Glucuronide Analogues of Retinoid O-Glucuronides and Their Preliminary in Vitro Breast Cancer" by Panigot et al., presented at the AAPS Annual Meeting and Exposition in San Antonio, Texas on Nov. 15-19, 1992.
"N-(4-Hydroxyphenyl)retinamide, A New Retinoid for Prevention of Breast Cancer in the Rat" by Moon et al., Cancer Research 39, pp. 1339-1346, Apr. 1979.
"Structure-Activity Relationships of Retinoids in Hamster Tracheal Organ Culture" by Newton et al., Cancer Research 40, pp. 3413-3425, Oct. 1980 by Laboratory of Chemoprevention, National Cancer Institute, Bethesda, Maryland 20205.
"Chemoprevention of Breast Cancer With Retinoids" by Veronesi et al., Journal of the National Cancer Institute Monographs, No. 12, pp. 93-97, 1992.
"Chemical Synthesis of all-trans retinoyl .beta.-glucuronide" by Barua et al., Journal of Lipid Research 26, pp. 1277-1282, 1985 by Department of Biochemistry and Biophysics, Iowa State University, Ames, IA 50011.
"Retinoids in Cancer Treatment" by Tallman et al., The Journal of Clinical Pharmacology 32, No. 10, pp. 868-888, Oct. 1992 by J.B. Lippincott Co., USA.
"Retinoids as Chemopreventive and Anticancer Agents in Intact Animals (Review)" by Hill et al., Anticancer Research 2, pp. 111-124, 1982 by Sourthern Research Institute, Box 3307-A, Birmingham, Alabama 35255.
"Growth Suppression of Human Breast Carcinoma Cells in Culture by N-(4-Hydroxyphenyl)retinamide and its Glucuronide and Through Synergism with Glucarate" by Bhatnager et al., Biochemical Pharmacology, 41, No. 10, pp. 1471-1477, 1991 by Pergamon Press, Great Britain.
"Therapeutic effect of N-(4-Hydroxyphenyl)retinamide on N-methyl-N-nitrosourea-induced Rat Mammary Cancer" by Dowlatshahi et al., Cancer Letters 47, pp. 187-192, 1989 by Elsevier Scientific Publishers Ireland Ltd.
"Effects of Retinoid Glucuronides on Mammary Gland Development in Organ Culture" by Mehta et al., Oncology 48, pp. 505-509, 1991 by S. Karger AG, Basel, Switzerland.
"Putative Metabolites Derived from Dietary Combinations of Calcium Glucarate and N-(4-Hydroxyphenyl)retinamide Act Synergistically to Inhibit the Induction of Rat Mammary Tumors by 7,12-dimethylbenz[.alpha.]anthracene" by Abou-Issa et al., Proc. Natl. Acad. Sci. USA 85, pp. 4181-4184, Jun. 1988.
"Effects of Pretreatment with the Retinoid N-(4-Hydroxyphenyl)-all-trans-retinamide and phenobarbital on the Disposition and metabolism of N-(4-Hydroxyphenyl)-all-trans-retinamide in Mice" by Hultin et al., Drug Metabolism and Disposition 16, No. 6, pp. 783-788, 1988.
"Biotransformation and Biological Activity of N-(4-Hydroxyphenyl)retinamide Derivatives in Rodents" by Swanson et al., The Journal of Pharmacology and Experimental Therapeutics 219, No. 3, pp. 632-637, 1981.
"Teratogenicity of N-(4-Hydroxyphenyl)-all-trans-retinamide in Rats and Rabbits" by Kenel et al., Teratogensis, Carcinogenesis, and Mutagenesis 8, pp. 1-11, 1988.
"In vitro interaction of fenretinide with plasma retinol-binding protein and its functional consequences" by Berni et al., Federation of European Biochemical Societies 308, No. 1, pp. 43-45, 1992.
"Tolerability of the Synthetic Retinoid Fenretinide (HPR)" by Costa et al., European Journal of Clinical Oncology 25, No. 5, pp. 805-808, 1989 by Pergamon Press, Great Britain.
"Pharmacokinetics of N-4-Hydroxyphenyl-retinamide and the effect of its oral administration on plasma retinol concentration in cancer patients" by Peng et al., Int. J. Cancer 43, p. 22-26, 1989.
"Induction of Differentiation of Human Promyelocytic Leukemia Cell Line HL-60 by Retinoyl Glucuronide, a Biologically Active Metabolite of Vitamin A" by Zile et al., Proc. Nat. Acad. Sci. USA 84, pp. 2208-2212, Apr. 1987 by Academic Press, Inc.
"Analysis of Water-Soluble Compounds: Glucuronides" by Barua, Arun B., Method Enzymol. 189, pp. 136-145, 1990.
"Synthesis of the D-glucuronic acid conjugates of N-(4-hydroxyphenyl)-and N-(2-hydroxyethyl)-retinamides" by Dawson et al., Carbohydrate Research 85, pp. 121-129, 1980 by Elsevier Scientific Publishing Co.
"Amino-Substituted .beta.-Benzyl-C-glycosides; Novel .beta.-Glycosidase Inhibitors" by Schmidt et al., Angew. Chem. Int. Ed. Engl. 30, No. 10, pp. 1328-1329, 1991.
"The Effective Charges at the Active Sites of Two Glycosidases" by Loeffler et al., J.C.S. Chem. Comm., pp. 984-985, 1974.
"A Review of the Methods of Chemical Synthesis of Sulphate and Glucuronide Conjugates" by Kaspersen et al., Xenobiotica, vol. 17, No. 12, pp. 1451-1471, 1987.
Hanessian, Stephen, et al., "Synthesis of Naturally Occuring C-Nucleosides, Their Analogues, and Funcionalized C-Glycosyl Presursors," Advances in Carbohydrate Chemistry and Biochemistry, vol. 33, 1976.
"The Chemistry and Biochemistry of C-Nucleosides and C-Aryglycosides" edited by Ellis et al., in Progress in Medicinal Chemistry 22, published by Elsevier Science Publishers, B.V. (Biomed. Div.) Oxford, 1985.
"Recent Developments in Synthesis of C-Glycosides" by Postema, Maarten H.D., in Tetrahedron Report Number 322, Mar. 12, 1992.
"N-Linked Analogs of Retinoid O-Glucuorindes" by Robarge, et al. Bioorganic & Medical Chemistry Letters vol. 4, No. 17, Aug. 1994, pp. 2117-2122.
"N-Linked Analogs of Retinoid O-Glucuorindes" by Robarge, et al. (Abstract) Am. Chemical 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 Symposium, Jul. 1994 (Abstract).
"Synthesis of N-Linked Glycoside Analogs of Retinoic Acid", by Robarge, et al., Am. Chem. Society, Aug. 21-25, 1994.
"N-and C-Glycoside Analogs of Retinoid O-Glucuronides and Their Breast Cancer Inhibitory Potential" by Panigot, et al., XIII Int. Symposium (Paris), Sep. 1994.
"Growth Suppression of Human Breast Carcinoma Cells in Culture by N-(4-Hydroxyphenyl) Retinamide and its Glucuronide and Through Synergism with Glucarate" by Bhatnager, et al., Biochemical Pharm., vol. 41, No. 10, 1991, pp. 1471-1477.
"Chemoprevention of Breast Cancer with Retinoids", Veronesi, et al., J. Nat. Can. Inst. Monographs, No. 12, 1992, pp. 93-97.
"Chemical Synthesis of All-Trans Retinoyl Betaglucuronide" by Barua, et al., J. Lipid Res., vol. 26, 1985, pp. 1277-1282.
"New Synthesis of C-substituted carbohydrates and their derivatives" by Yu, et al., Abstract of Dorklady Akad. Nank. SSSR, 129, 1049-52 (1959) CA:54-8611e (1960).
"Preparation of a glucopyranosylbenzene derivative" by Gerecs, et al., CA:52-11778g (1958) Abstract of Acta Chem. Acad. Sci. Hung. 13, 231-2 (1957).

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