Therapeutically active compounds based on indazole...

C - Chemistry – Metallurgy – 07 – D

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C07D 231/56 (2006.01) A61K 31/415 (2006.01) A61K 31/416 (2006.01)

Patent

CA 2309175

Therapeutically active compositions of matter are described which are useful for treating or preventing diseases and conditions comprising inflammatory diseases including joint inflammation, Crohn's disease, and inflammatory bowel disease; respiratory diseases such as chronic obstructive pulmonary disease (COPD) including asthma, chronic bronchitis, and pulmonary emphysema; infectious diseases including endotoxic shock and toxic shock syndrome; immune diseases including systemic lupus erythematosis and psoriasis; and other diseases including bone resorption diseases and reperfusion injury; wherein said composition of matter comprises a compound which is an inhibitor of phosphodiesterase isozyme 4 (PDE4) and wherein an indazole is one essential component of said compound's overall chemical structure, and wherein said indazole constitutes a bioisosteric replacement of a catechol component or functional derivative thereof in a known compound having the same said therapeutic activity and the same remaining said components of its overall chemical structure. Included are compounds of Formula (IA) or (IB), wherein R2a and R2b are independently selected from the group consisting essentially of hydrogen and hereinafter recited substituents, provided that one, but not both of R2a and R2b must be independently selected as hydrogen, wherein said substituents comprise moieties including the following: (IC), (ID), (IE), (IF), (IIA), (IIB), (IIC), (IID), (IIE), (IIF), (IIG), (IIH), (III), (IIIA), (IIIB), (IIIC), (IIID), (IIIE), (IIIF), (IIIG), (IIIH), (IIII), (IIIJ), (IIIK), (IIIL), (IIIM), (IIIN), (IIIO), (IIIP), (IIIQ), (IIIR), (IIIS), (IIIT), (IV), (VA), (VB), (VC), (VD), (VEa), (VE), (VF), (VG), (VH), (VI), (VJ), (VK), (VL), (VM).

L'invention se rapporte à des compositions thérapeutiquement actives qui s'avèrent utiles pour traiter ou prévenir des maladies et des troubles, et notamment des maladies inflammatoires telles que l'inflammation des articulations, la maladie de Crohn, et les maladies intestinales inflammatoires; des maladies respiratoires telles que les maladies obstructives respiratoires (MOR) et notamment l'asthme, la bronchite chronique et l'emphysème pulmonaire; des maladies infectieuses et notamment le syndrome de choc endotoxique et toxique staphylococcique; des maladies immunitaires et notamment le lupus érythémateux disséminé et le psoriasis; et d'autres maladies telles que les maladies de résorption osseuse et les lésions dues aux perfusions répétées. La composition de cette invention comporte un composé qui est un inhibiteur de l'iso-enzyme phosphodiestérase (PDE4). Un composant essentiel de la structure chimique globale dudit composé est un indazole qui est un élément de remplacement bio-isostère d'un composant catéchol ou d'un de ses dérivés fonctionnels dans un composé connu possédant la même activité thérapeutique et les mêmes composants restants de sa structure chimique globale. L'invention se rapporte à des composés représentés par les formules (IA) et (IB), dans lesquelles R?2¿¿a? et R?2¿¿b? sont indépendamment sélectionnés dans le groupe constitué principalement par l'hydrogène et les substituants décrits ci-après, à condition qu'un seul des deux éléments que sont R?2¿¿a? et R?2¿¿b?, et non les deux, soit indépendamment sélectionné comme l'hydrogène, lesdits substituants comportant des fractions représentées par les formules (IC), (ID), (IE), (IF), (IIA), (IIB), (IIC), (IID), (IIE), (IIF), (IIG), (IIH), (III), (IIIA), (IIIB), (IIIC), (IIID), (IIIE), (IIIF), (IIIG), (IIIH), (IIII), (IIIJ), (IIIK), (IIIL), (IIIM), (IIIN), (IIIO), (IIIP), (IIIQ), (IIIR), (IIIS), (IIIT), (IV), (VA), (VB), (VC), (VD), (VE¿a?), (VE), (VF), (VG), (VH), (VI), (VJ), (VK), (VL), (VM).

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