Tricyclic-bis-enone derivatives and methods of use thereof

Details Tricyclic-bis-enone derivatives and methods of use thereof Tricyclic-bis-enone derivatives and methods of use thereof

C - Chemistry, Metallurgy

07

C

C07C 255/47 (2006.01) A61K 31/122 (2006.01) A61K 31/19 (2006.01) A61K 31/215 (2006.01) A61K 31/277 (2006.01) A61P 35/00 (2006.01) C07C 49/603 (2006.01) C07C 49/737 (2006.01) C07C 62/38 (2006.01) C07C 69/757 (2006.01) C07C 271/18 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2472581

Novel tricyclic-bis-enone derivatives (TBEs) as well as the process for the preparation of such TBEs are provided. Also provided are methods for prevention and/or treatment of cancer, Alzheimer's disease, Parkinson's disease, multiple sclerosis, amyotropic lateral sclerosis, rheumatoid arthritis, inflammatory bowel disease, and all other diseases whose pathogenesis is believed to involve excessive production of either nitric oxide (NO) or prostaglandins or the overexpression of iNOS or COX-2 genes or gene products. Further, methods for the synthesis of the TBE compounds of the invention utilize cheap commercially available reagents and are highly cost effective and amenable to scale-up. Additional high efficiency synthetic methods that utilize novel intermediates as well as the synthesis of these intermediates are also provided. Furthermore, the invention also provides methods for designing novel and water-soluble TBEs.

Cette invention concerne des nouveaux dérivés de bis-énone tricyclique (TBE) ainsi que leur procédé de fabrication. Sont également décrites de méthodes de prévention et/ou de traitement du cancer, de la maladie d'Alzheimer, de la maladie de Parkinson, de la sclérose en plaques, de la sclérose latérale amyotropique, de la polyarthrite rhumatoïde, de la maladie intestinale inflammatoire et de toutes les autres pathologies qui semblent impliquer une production excessive soit d'oxyde nitrique (NO), soit de prostaglandines, ou bien une surexpression de gènes ou de produits géniques iNOS ou COX-2. L'invention concerne également des procédés de synthèse des composés TBE de l'invention qui reposent sur l'emploi de réactifs bon marché, disponibles dans le commerce, qui présent un bon rapport qualité-prix et qui peuvent faire l'objet d'une fabrication à grande échelle. L'invention concerne également des procédés de synthèse hautement efficaces ainsi que la synthèse de ces intermédiaires. De plus, l'invention porte sur des méthodes de conception de TBE nouveaux et hydrosolubles.

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