(-)-verbenone derivatives

C - Chemistry – Metallurgy – 07 – C

Patent

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Details

C07C 235/62 (2006.01) A61K 31/13 (2006.01) A61K 31/15 (2006.01) A61K 31/16 (2006.01) A61P 11/08 (2006.01) C07C 45/34 (2006.01) C07C 45/74 (2006.01) C07C 49/683 (2006.01) C07C 69/732 (2006.01) C07C 69/738 (2006.01) C07C 225/20 (2006.01) C07C 251/42 (2006.01) C07C 251/60 (2006.01) C07C 275/38 (2006.01) C07D 295/02 (2006.01) C07D 295/033 (2006.01) C07D 295/14 (2006.01) C07D 295/155 (2006.01)

Patent

CA 2367367

A description is given here of novel solid and stable derivatives of (-)- verbenone having formula (I) wherein, when X = O Z = H, =CHAr, =C(OH)COOEt, =NOR; Y = H, NH2, NH3+ X1-, NHCOAr, NHCOR, NHCONHR, NHCONHAr; X1- = pharmaceutically acceptable anion; Ar = aryl or heteroaryl, preferably phenyl, 4-chlorophenyl, 2-furyl, 2-thienyl, 2-hydroxyphenyl, 2-acetoxyphenyl; R = H, C1-C4 alkyl, C4-C6 cycloalkyl, CH2COOH, CH2COOEt, CH2COCH3, CH2CN, CH2COCH2COOEt, CH2C6H5; and, when X = dimethylamino, diethylamino, pyrrolidino, piperidino or morpholino: Y = H; Z = H, CONHAr, CONHR; Ar = aryl, preferably phenyl; R = H, C1-C4 alkyl, C4-C6 cycloakyl. A description is also given of the processes for the preparation of these derivatives and of the novel intermediates used in those processes. The novel derivatives are characterized by their solubility in water; some of them also have a high anti- inflammatory activity.

L'invention concerne de nouveaux dérivés solides et stables de (-)-verbénone de formule, dans laquelle, lorsque X = O, Z = H, =CHAr, =C(OH)COOEt, =NOR; Y = H, NH¿2?, NH¿3??+¿X¿1??-¿, NHCOAr, NHCOR, NHCONHR, NHCONHAr; X¿1??-¿= anion pharmaceutiquement acceptable; Ar = aryle ou hétéroaryle, de préférence phényle, 4-chlorophényle, 2-furyle, 2-thiényle, 2-hydroxyphényle, 2-acétoxyphényle; R = H, C¿1?-C¿4? alkyle, C¿4?-C¿6? cycloalkyle, CH¿2?COOH, CH¿2?COOEt, CH¿2?COCH¿3?, CH¿2?CN, CH¿2?COCH¿2?COOEt, CH¿2?C¿6?H¿5?; et, lorsque X = diméthylamino, diéthylamino, pyrrolidino, pipéridino ou morpholino: Y = H; Z = H, CONHAr, CONHR; Ar = aryle, de préférence phényle; R = H, C¿1?-C¿4? alkyle, C¿4?-C¿6? cycloalkyle. L'invention traite également des procédés de préparation de ces dérivés et des nouveaux intermédiaires utilisés dans ces procédés. Les nouveaux dérivés se caractérisent par leur solubilité dans l'eau, certains d'entre eux présentant une activité anti-inflammatoire élevée.

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