Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2006-07-18
2006-07-18
McKane, Joseph K. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S483000, C548S484000
Reexamination Certificate
active
07078427
ABSTRACT:
Novel compounds useful as chemotherapeutic and chemopreventive agents are provided. The compounds are analogs of indole-3-carbinol metabolites wherein the structures and substituents of the compounds are selected to enhance the compounds' overall efficacy, particularly with respect to therapeutic activity, oral bioavailability, long-term safety, patient tolerability, and therapeutic window. The compounds are useful not only in treatment of cancer but also in prevention of cancer. One preferred class of the novel compounds have the structure of formula (I)wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12are defined herein. Pharmaceutical compositions are provided as well, as are methods of synthesis and use.
REFERENCES:
patent: 3527517 (1970-09-01), Hackmann
patent: 4636820 (1987-01-01), Schmidt et al.
patent: 5086171 (1992-02-01), Mathiaparanam
patent: 5116978 (1992-05-01), Mathiaparanam
patent: 5206377 (1993-04-01), McAfee
patent: 5266699 (1993-11-01), Naef et al.
patent: 5326879 (1994-07-01), Takahashi et al.
patent: 5380723 (1995-01-01), Takahashi et al.
patent: 5843607 (1998-12-01), Hu et al.
patent: 5942340 (1999-08-01), Hu et al.
patent: 5948808 (1999-09-01), Safe
patent: 6323233 (2001-11-01), Wright et al.
patent: 6407102 (2002-06-01), Mahboobi et al.
patent: 0908787 (1999-04-01), None
patent: 2207670 (1989-02-01), None
patent: WO 99/57117 (1999-11-01), None
patent: WO 02/36561 (2002-05-01), None
patent: WO 02/36597 (2002-05-01), None
Fuerstner et al., 1995, CAS: 123:83146.
Black et al., 1993, CAS: 119:271129.
Pindur et al., 1987, CAS:107:217419.
Chu et al., 1984, CAS:102:184940.
Brieskorn et al., 1979, CAS :93 :71451.
Hindo et al., 1974, CAS :82 :111897.
Suzuki et al., 1973, CAS :80 :59818.
Hill et al., 1972, CAS :77 :5277.
Aygüun et al. (2003), “Synthesis and Biological Evaluation of Structural Variants of Carbazoquinocin C,”Journal of Heterocyclic Chemistry40(3):411-417.
Black et al. (1993), “Calix[3]indoles, New Macrocyclic Tris(indolylmethylene) Compounds with 2,7-Linkages,” J. Chem. Soc., Chem. Commun., 10:819-821.
Black et al. (1995), “Synthesis of Indolo[3,2-b]carbazoles from 4,6-Dimethoxyindole and Aryl Aldehydes,”Tetrahedron 51(43):11801-11808.
Hino et al. (1973), “Preparation of 3-Substituted 2-Indolinethiones via Diindolyl Disulfides. Reaction of 3-Substituted Indoles with Sulfur Monochloride,”Chemical&Pharmaceutical Bulletin 21(12):2739-2748 abstract only).
Hino et al. (1974), “Reaction of Skatole with Iodine in the Presen ce of Thiourea,”Chemical&Pharmaceutical Bulletin 22(11): 2728-2731 (abstract only).
Hünig et al. (1976), “Synthese Vinyloger und Azavinyloger Redoxsysteme Mit Indolylresten Als Endgruppen,”Liebigs Ann. Chem. 6:1039-1059.
Jackson et al. (1987), “Electrophilic Substitution in Indoles. Part 15. The Reaction Between Methylenedi-indoles and p-Nitrobenzenediazonium Fluoroborate,”J. Chem. Soc. Perkin Trans. l 11:2543-2551.
Lau et al. (1986), “Reductive Deoxygenation of Aryl Aldehydes and Ketones and Benzylic, Allylic, and Tertiary Alcohols by Znl2-NaCNBH3,”J. Org. Chem. 51(15):3038-3043.
Napolitano et al. (1993), “Oxidation Chemistry of 5,6-Dihydroxy-2-methylindole,”Tetrahedron 49(40):9143-9150.
Pindur et al. (1987), “Reaktivität und Reaktionswege von Methylsubstituierten Bisindolylcarbenium-Ionen,”Journal of Heterocyclic Chemistry 24(1):159-163.
Von Dobeneck et al. (1969), “αβ'-Diindolylmethane und -Methene. Der Urorosein-Chromophor,”Chemische Berichte. 102(4):1347-1356.
Wille et al. (2001), “Malassezin—A Novel Agonist of the Arylhydrocarbon Receptor from the YeastMalassezia furfur,” Bioorganic&Medicinal Chemistry 9:955-960.
Biswas et al. (1998), “A Convenient Synthesis of 5,11-Dihydro-5,11-dimethyl-6-trifluoromethylindolo[3,2-b]carbazole,”Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry 37B(9):841-843.
Bonnesen et al. (2001), “Dietary Indoles and Isothiocyanates That Are Generated from Cruciferous Vegetables Can Both Stimulate Apoptosis and Confer Protection Against DNA Damage in Human Colon Cell Lines,”Cancer Research 61:6120-6130.
Bradlow et al. (1991), “Effects of Dietary Indole-3-carbinol on Estradiol Metabolism and Spontaneous Mammary Tumors in Mice,”Carcinogenesis 12(9):1571-1574.
Chinni et al. (2001), “Indole-3-carbinol (13C) Induced Cell Growth Inhibition, G1 Cell Cycle Arrest and Apoptosis in Prostate Cancer Cells,”Oncogene 20:2927-2936.
Grotta et al. (1961), “Preparation of Some Condensed Ring Carbazole Derivatives,”J. Org. Chem. 26:1509-1511.
Kistenmacher et al. (1992), “Direct Synthesis of IndolocarbazolesviaNew Dinitroterphenyl Precursors,”J. Heterocyclic Chem. 29:1237-1239.
Knölker et al. (1998), “Iron-Mediated Synthesis of Indolo[2,3-b]carbazole,”Tetrahedron Letters 39:4007-4008.
Knölker et al. (2000), “Transition Metal Complexes in Organic Synthesis. Part 61: Convergent Synthesis of Indolo[2,3-b]carbazole by an Iron-Mediated Bidirectional Annulation of Two Indole Rings,”Tetrahedron 56:4733-4737.
Kojima et al. (1994), “Chemoprevention of Spontaneous Endometrial Cancer in Female Donryu Rats by Dietary Indole-3-carbinol,”Cancer Research 54:1446-1449.
Liu et al. (1994), “Indolo[3,2-b]carbazole: A Dietary-Derived Factor That Exhibits Both Antiestrogenic and Estrogenic Activity,”Journal of the National Cancer Institute 86(23):1758-1765.
Michnovicz et al. (1997), “Changes in Levels of Urinary Estrogen Metabolites After Oral Indole-3-carbinol Treatment in Humans,”Journal of the National Cancer Institute 89(10):718-723.
Swindells et al. (1956), “Preparation of Indolocarbazoles. VIII. Preparation of 1-Methylindolo[2',3'-2,3]carbazole,”J. Chem. Soc.,pp. 1135-1138.
Veronesi, U.; Bonanni, B. “Chemoprevention; From research to clinical oncology,”European Journal of Cancer, 41 (2005) 1833-1841.
Crowell, J. “The chemopreventative agent development research program in the Division of Cancer Prevention of the US National Cancer Institute: An overview,”European Journal of Cancer, 41 (2005) 1889-1910.
Marshall, K. “Cervical Dysplasia: Early Intervention,”Alternative Medicine Review, 8 (2003) 156-170.
Kim, Y.; Milner, J. “Targets for indole-3-carbinol in cancer prevention,”Journal of Nutritional Biochemistry16 (2005) 65-73.
Abstract: Manson, M.; Farmer, P.; Gescher, A.; Steward, W. “Innovative agents in cancer prevention,”Recent Results Cancer Res., 166 (2005) 257-75.
Chao Wan-Ru
Jong Ling
McKane Joseph K.
Reed Intellectual Property Law Group
Shiao Robert
SRI - International
LandOfFree
Analogs of indole-3-carbinol metabolites as chemotherapeutic... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Analogs of indole-3-carbinol metabolites as chemotherapeutic..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Analogs of indole-3-carbinol metabolites as chemotherapeutic... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3569312