Curcumin analogs with anti-tumor and anti-angiogenic properties

Patent 6664272 Issued on December 16, 2003. Estimated Expiration Date:

December 4, 2020. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Abstract Claims Description Full Text

Patent References

3114775

3911129

Substituted thiopyrano(4,3-b)pyrans
Patent #: 4127667
Issued on: 11/28/1978
Inventor: Rovnyak

Use of ଱,଱-bis(dialkylaminobenzylidene) ketone dyes in optical recording elements
Patent #: 4415621
Issued on: 11/15/1983
Inventor: Specht , et al.

Spectral sensitizing dyes in photopolymerizable systems
Patent #: 4755450
Issued on: 07/05/1988
Inventor: Sanders , et al.

Photoinitiator and photopolymerizable composition using the same
Patent #: 4987057
Issued on: 01/22/1991
Inventor: Kaji, et al.

Pharmaceutical compounds
Patent #: 5700804
Issued on: 12/23/1997
Inventor: Collins, et al.

Photoinitiator compositions including amino acids, coumarin and titanocene and photosensitive materials using the same
Patent #: 5811218
Issued on: 09/22/1998
Inventor: Kaji, et al.

Pharmaceutical piperazine compounds
Patent #: 5852018
Issued on: 12/22/1998
Inventor: Bryans, et al.

Chemical functionalization of surfaces Patent #: 6022597
Issued on: 02/08/2000
Inventor: Yan, et al.

Inventors

Assignee

Emory University

Application

No. 09/729662 filed on 12/04/2000

US Classes:

514/327, Chalcogen bonded directly to ring carbon of the piperidine ring514/151, Acyclic C-N=N-N containing514/210.2, The additional hetero ring contains ring nitrogen514/252.14, The additional hetero ring is a 1,3 diazine ring514/252.18, Additional six-membered hetero ring consisting of five ring carbons and one ring nitrogen attached directly or indirectly to the 1,3-diazine by nonionic bonding514/255.06, Nitrogen or -C(=X)-, wherein X is chalcogen, bonded directly to ring carbon of the 1,4-diazine ring514/256, 1,3-diazines (e.g., pyrimidines, etc.)514/304, Tropanes (including nor or dehydro form)514/318, The additional ring is a six-membered hetero ring consisting of one nitrogen and five carbon atoms514/332, Plural six-membered hetero rings consisting of one nitrogen and five carbon atoms514/333, Additional hetero ring other than the six-membered hetero rings514/432, The hetero ring is six-membered514/460, Chalcogen bonded directly to ring carbon of the hetero ring544/295, Plural diazine rings544/296, Plural 1,3-diazine rings546/216, Chalcogen bonded directly to ring carbon of the piperidine ring549/28, Chalcogen or nitrogen attached directly to the hetero ring by nonionic bonding549/416, Chalcogen bonded directly to the hetero ring552/1, Azides568/327Bicyclo ring system

Examiners

Primary: Shah, Mukund J.
Assistant: Balasubramanian, Venkataraman

Attorney, Agent or Firm

Alston & bird LLP

International Classes

C07C 225/22 (20060101)
C07C 317/00 (20060101)
C07C 235/34 (20060101)
C07C 235/00 (20060101)
C07C 251/40 (20060101)
C07C 251/00 (20060101)
C07C 49/697 (20060101)
C07C 321/00 (20060101)
C07C 275/24 (20060101)
C07C 49/255 (20060101)
C07C 49/753 (20060101)
C07C 49/248 (20060101)
C07C 321/20 (20060101)
C07C 275/00 (20060101)
C07D 209/00 (20060101)
C07C 49/747 (20060101)
C07C 49/233 (20060101)
C07C 49/235 (20060101)
C07D 209/34 (20060101)
C07C 49/00 (20060101)
C07C 45/29 (20060101)
C07D 451/00 (20060101)
C07C 225/00 (20060101)
C07C 317/10 (20060101)
C07C 45/00 (20060101)
C07C 45/62 (20060101)
C07D 295/205 (20060101)
C07D 213/00 (20060101)
C07C 45/74 (20060101)
C07D 317/00 (20060101)
C07D 317/50 (20060101)
C07D 213/63 (20060101)
C07D 451/02 (20060101)
C07D 295/00 (20060101)

Abstract

The present invention is directed to curcumin analogs exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

Other References

Zheng et al Zhongguo Yiyao Gonye Zazhi, 28(5), 230231, 1997, CA 115: 102878, 1991.
Gutkowska et al., Acta Poloniae Pharmaceutica, 46(3): 212-18, 1989, CA112: 216649, 1990.
Gutkowska et al., Acta Poloniae Pharmaceutica, 42(5): 437-41, 1985, CA 107: 115819, 1987.
Ojima et al., Bull. Chem. Soc. Jpn, 50(6), 1522-1526, 1977. CA 87: 20055, 1977.
Shoppee et al., J. Chem. Soc. Perkin Trans. I 9, 1028-1030, 1977. CA 87: 102029, 1977.
Fujisaki et al. JP 62225562. CA: 108: 77360, 1988.
Keinan et al., J. Org. Chem. 48(26), 5302-9, 1983.
Pivnenko et al., Zh. Org. Khim. 11(12), 2527-2533, 1975. CA 84:73234, 1976.
Pivnenko et al., Zh. Obshch. Khim. 42(5), 1096-1102, 1972. CA 72: 513251, 1972.
Cremlyn et al., "The Synthesis and Chlorosulfonation of Some Diarylidene and Heteroarylidene Ketones with Varying Alicyclic Ring Size", Phosphorus, Sulfur, and Silicon, 1995, pp. 205-217, vol. 107
Hammam et al., "Synthesis and Anti-Cancer Activity of Pyridine and Thiazolopyrimidine Derivatives Using 1-Ethylpiperidone as a Synthon", Indian J. of Chem., 2001, pp. 213-221, vol. 40B
Li et al., "Samarium (III) Iodide Promoted Preparation of ଱,଱'--bis(substituted benzylidene) cyclohexanones from benzaldehydes and cyclohexanone", J. Chem. Research (S), 2000, pp. 580-581
Mahfouz et al., "Synthese mehrfach oxigenierter 2-Hydroxyxanthone", Arch. Pharm. (Weinheim), 1990, pp. 163-169, vol. 323
Nakano et al., "A Convenient Synthesis of ଱,଱'--Bis(substitutedbenzylidene)cycloalkanones", Chemistry Letters, 1993, pp. 2157-2158
Wiemer et al., "Vidalols A and B, new anti-inflammatory bromophenols from the Caribbean marine red alga Vidalia obtusaloba", Experientia, 1991, pp. 851-853, vol. 47
Artico, et al., "Genometrically and Conformationally Restrained Cinnamoyl Compounds as Inhibitors of HIV-1 Integrase: Synthesis, Biological Evaluation, and Molecular Modeling", J. Med. Chem., 1998, pp. 3948-3960, vol. 41, No. 21
Dinkova-Kostova, et al., "Chemoprotective Properties of Phenylpropenoids, Bis(benzylidene)cycloalkanones, and Related Michael Reaction Acceptors: Correlation of Potencies as Phase 2 Enzyme Inducers and Radical Scavengers", J. Med. Chem., 1998, pp. 5287-5296, vol. 41, No. 26
El-Subbagh, et al., "Synthesis and Biological Evaluation of Certain ଱,ଲ-Unsaturated Ketones and Their Corresponding Fused Pyridines as Antiviral and Cytotoxic Agents", J. Med. Chem., 2000, pp. 2915-2921, vol. 43, No. 15
Sun, et al., "Design, Synthesis, and Evaluations of Substituted 3-[3-or 4-Carboxyethylpyrrol-2-yl)methylidenyl]indolin-2-ones as inhibitors of VEGF, FGF, and PDGF Receptor Tyrosine Kinases", J. Med. Chem., 1999, pp. 5120-5130, vol. 42, No. 25
Sun, et al., "Identification of Substituted 3-[(4,5,6,7-Tetrahydro-1H-indol-2-yl)methylene]-1,3-dihydroindol-2-ones as Growth Factor Receptor Inhibitors for VEFG-R2 (Flk-1/KDR), FGF-R1, and PDGF-R^ଲ Tyrosine Kinases", J. Med. Chem., 2000, pp. 2655-2663, vol. 43, No. 14
Sun, et al., "Synthesis and Biological Evaluations of 3-Substituted Indolin-2-ones: A Novel Class of Tyrosine Kinase Inhibitors That Exhibit Selectivity toward Particular Receptor Tyrosine Kinases", J. Med. Chem., 1998, pp. 2588-2603, vol. 41, No. 14
Teuscher, "Potentiell antiangiogene Substanzen aus der Gruppe der ଱, ଱'-Bis(amidinobenzyl)cycloalkanon-Derivate and ଱-(Arylsulfonylamino)-ω-phenylcarbonsaure-4-amidinoanilide", Pharmazie, 1987, pp. 109-110, vol. 42, H.2
Thaloor, et al., "Inhibition of Angiogenic Differentiation of Human Umbilical Vein Endothelial Cells by Curcumin", Cell Growth & Differentiation, 1998, pp. 305-312, vol. 9
Vieth, et al., "DoMCoSAR: A Novel Approach for Establishing the Docking Mode That Is Consistent with the Structure-Activity Relationship. Application to HIV-1 Protease Inhibitors and VEGF Receptor Tyrosine Kinase Inhibitors", J. Med. Chem., 2000, pp. 3020-3032, vol. 43, No. 16