Preparation and the use of ethoxy combretastatins and their...

Details Preparation and the use of ethoxy combretastatins and their... Preparation and the use of ethoxy combretastatins and their...

2007-05-16

2010-11-23

Davis, Brian J (Department: 1621)

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

Organic compounds

Oxygen containing

C568S011000, C568S015000, C568S586000, C568S644000, C568S646000, C564S158000, C564S194000, C564S196000, C514S077000, C514S114000, C514S616000, C514S617000, C514S619000, C514S620000, C514S626000, C514S721000

Reexamination Certificate

active

07838706

ABSTRACT:
The invention disclosed a total synthesis process of novel ethoxy combretastatins and their prodrugs. Combretastatins are chemically modified by ethoxy substituted on the 4′-position of their B aryl ring and are converted to be their soluble prodrugs of phosphate or their inner salt of phosphorylcholine by modifying the hydroxyl on the 3′-position of their B aryl ring. Similarly, 3′-amino combretastatin is 4′-ethoxy chemically modified and further side chain of amino acid can be introduced to the amino to form soluble prodrug of amino acidamide. The structure of the said compound is showed as formula (I). Ethoxy combretastatins possess potent tubulin polymerization inhibitory activity and can be used for the treatment of inhibiting tumor or neovascular.

REFERENCES:
patent: 5430062 (1995-07-01), Cushman et al.
patent: 5674906 (1997-10-01), Hatanaka et al.
Kim et al., Chemical & Pharmaceutical Bulletin (2003), 51(5), p. 516-521.
International Search Report of PCT/CN2007/070020, dated Aug. 2, 2007.
Pettit et al. “Isolation, Structure, and Synthesis of Combretastatins A-1 and B-1, Potent New Inhibitors of Microtubule Assembly, Derived fromCombretum caffrum.” Journal of Natural Products, vol. 50(1) Jan.-Feb. 1987, pp. 119-131.
Pettit et al. Isolation, structure, and synthesis of combretastatin A-2, A-3 and B-2. Can. J. Chem. vol. 65, 1987, pp. 2390-2396.
Pettit et al. Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4. Experientia, 45, 1989, pp. 209-211.
Cushman et al. “Synthesis and Evaluation of Analogues of (Z)-1-(4-Methoxyphenyl)-2-(3,4,5-thrimethoxyphenyl)ethane as Potential Cytotoxic and Antimitotic Agents.” Journal of Medicinal Chemistry, cil 35(12), 1992, pp. 2293-2307.
Pettit et al. Antineoplastic Agents. 291. Isolation and Synthesis of Combretastatins A-4, A-5, and A-6. J. Med. Chem., 38, 1995. pp. 1666-1672.
Thorpe. “Vascular Targeting Agents as Cancer Therapeutics.” Clinical Cancer Research, vol. 10, Jan. 15, 2004, pp. 415-427.
West et al. Combretastatin A4 phosphate. Anit-Cancer Drugs, vol. 15(3), 2004. pp. 179-187.
Young et al. “Combretastatin A4 phosphate: background and current clinical status.” Expert Opin. Investig. Drugs vol. 13(9), 2004, pp. 1171-1182.

Affiliated with

Also associated with

Rating

Preparation and the use of ethoxy combretastatins and their... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Preparation and the use of ethoxy combretastatins and their..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation and the use of ethoxy combretastatins and their... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4158524