Curcumin analogues and uses thereof

Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfur containing

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C568S325000, C514S544000

Reexamination Certificate

active

07355081

ABSTRACT:
The present invention relates to compounds capable of acting as androgen receptor antagonists, pharmaceutical formulations containing the same, and methods of use thereof. Such uses include, but are not limited to, use as antitumor agents, particularly for the treatment of cancers such as colon, skin and prostate cancer and to induce androgen receptor antagonist activity in a subject afflicted with an androgen-related affliction. Examples of androgen-related afflictions include, but are not limited to, baldness, hirsutism, behavioral disorders, acne, and uninhibited spermatogenesis wherein inhibition of spermatogenesis is so desired.

REFERENCES:
patent: WO 95/18606 (1995-06-01), None
patent: WO 97/16403 (1997-05-01), None
patent: WO 99/22728 (1999-05-01), None
patent: WO 01/30335 (2001-05-01), None
patent: WO 01/40188 (2001-06-01), None
Ohtsu et al. “Anti-Tumor Agents 222. Synthesis and Anti-androgen Activity of New Diarylheptanoids” Biorganic & Medicinal Chemistry 11: 5083-5090 (2003).
Anto et al; “Anti-tumour and free radical scavenging activity of synthetic curcuminoids”International Journal of Pharmaceutics. 131 1-7 (1996).
Berzin et al; “Identification of natural curcumins”Bioorganicheskaya Khirniya. 22: 10-11 823-831 (1996).
Chowdhury et al; “Isolation, characterization and insect growth inhibitory activity of major turmeric constituents and their derivatives againstSchistocerca gregaria(Forsk) andDysdercus koenigii(Walk)”Pest Management Science. 56 1086-1092 (2000).
Hahm et al; “New and known symmetrical curcumin derivatives inhibit the formation of Fos-Jun DNA complex”Cancer Letters. 184 89-96 (2000).
Masuda et al; “Antioxidative Curcuminoids from Rhizomes ofCurcuma Xanthorrhiza” Phytochemistry. 31:10 3645-3647 (1992).
Ohtsu et al; “Antitumor Agents 217 Curcumin Analogues as Novel Androgen Receptor Antagonists with Potential as Anti-Prostate Cancer Agents”Journal of Medicinal Chemistry. 45 5037-5042 (2002).
European Search Report for 03718072.6-1521/US0309350. Date of mailing May 10, 2005.
Arbiser, Jack L., et al., Curcumin is an In Vivo Inhibitor of Angiogenesis,Molecular Medicine, vol. 4, pp. 376-383 (1998).
Choshi et al., Synthesis of Dibenzoylmethane Derivatives and Inhibition of Mutagenicity in Salmonella Typhimurium,Chem. Abstract., vol. 117, No. 48036 (1992).
Gorbitz, C.H. et al., Structural Studies of Curcuminoids, V. Crystal Structures of 1,7,-bis (3, 4-dimethoxyphenyl)-4-benzyl-1, 6-heptadiene-3, 5-dione and 1,7-bis (4-hydroxy-3 methoxyphenyl)-4-(2-oxo-2-ethoxyethyl)-1, 6-heptadiene-3, 5-dione,Chem. Abstract., vol. 107, No. 6988 (1986).
Ishida, Junko, et al., Antitumor-promoting effects of cyclic diarylheptanoids on Epstein-Barr virus activation and two-stage mouse skin carcinogenesis,Cancer Letters, vol. 159, pp. 135-140 (2000).
Martono, S., Inhibitory Effects of Curcumin and its Analogs on In Vitro Rat Liver Glutathione S-Transferases Activity,Chem. Abstract., vol. 128, No. 110377 (1996).
McDonald et al., Synthesis and Anticancer Activity of nordihydrogualaretic Acid and Analogues,Chem. Abstract., vol. 138, No. 362138 (2001).
Nurfina, A. N., et al., Synthesis of some symmetrical curcumin derivatives and their anti-inflammatory activity,Eur. J. Med. Chem., vol. 32, pp. 321-328, (1997).
Parveen, I., et al., Labeled Compounds of Interest as Antitumor Agents,Chem. Abstract., vol. 133, No. 281645 (2000).
Pedersen et al., Synthesis of Naturally Occurring Curcuminoids and Related Compounds,Chem. Abstract., vol. 103, No. 178092 (1985).
Ruby, A.J., et al., Anti-tumour and antioxidant activity of natural curcuminoids,Cancer Letters, vol. 94, pp. 79-83 (1995).
Suglyama, Yasunori, et al., Involvement of the β-Diketone Moiety in the Antioxidantive Mechanism of Tetrahydrocurcumin,Biochemical Pharmacology, vol. 52, pp. 519-525 (1996).
Syu, Wan-Jr., et al., Cytotoxicity of Curcuminoids and Som Novel Compounds from Curcuma zedoaria,J. Nat. Prod., vol. 61, pp. 1531-1534 (1998).
International Search Report corresponding to PCT/US03/09350 dated Dec. 19, 2003.
International Search Report for Application No. PCT/US2005/36522 mailed on Apr. 24, 2006.
Devasena et al. “Bis-1,7-(2-Hydroxyphenyl)-Hepta-1,6-Diene-3,5-Dione (A Curcumin Analog) Ameliorates DMH-Induced Hepatic Oxidative Stress During Colon Carcinogenesis”Pharmacological research43(1): 39-45 (2002).
Sakano et al. “Metal-Mediated DNA Damage Induced by Curcumin in the Presence of Human Cytochrome P450 Isozymes”Archives of Biochemistry and Biophysics405: 223-230 (2002).
Ishida et al. “Antitumore Agents. Part 214: Synthesis and Evaluation of Curcumin Analogues as Cytotoxic Agents”Bioorganic&Medicinal Chemistry10: 3481-3487 (2002).
Ireson et al. “Characterization of Metabolites of the Chemopreventive Agent Curcumin in Human and Rat Hepatocytes and in the Rat in Vivo, an Evaluation of Their Ability to Inhibit Phorbol Ester-Induced Prostaglandin E2Production”Cancer Research61: 1058-1064 (2001).
Ahsan et al. “Pro-oxidant, Anti-oxidant and Cleavage Activities on DNA of Curcumin and its Derivatives Demethoxycurcumin and bisdemethoxycurcumin”Chemico-Biological Interactions121: 161-175 (1999).
Anto et al. “Anti-Tumore and Free Radical Scavenging Activity of Synthetic Curcuminoids”International journal of Pharmaceutics131: 1-7 (1996).
Ohtsu et al. “Antitumore Agents 222. Synthesis and Anti-androgen Activity of New Diarylheptanoids”Bioorganic&Medicinal Chemistry11: 5083-5090 (2003).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Curcumin analogues and uses thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Curcumin analogues and uses thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Curcumin analogues and uses thereof will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2748423

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.