Oxy-and amino-substituted tetrahydrofuryl derivatives with...

C - Chemistry – Metallurgy – 07 – D

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C07D 307/22 (2006.01) A61K 31/341 (2006.01) A61P 35/00 (2006.01)

Patent

CA 2400612

Compounds of formula (I) wherein the substituent groups defined by R1, R2, R3 and R4 are each independently selected of H, C(=O) R,P(=O)R'R",S(=O)R'R", substituted or unsubstituted C1- C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl; wherein each of the R', R" groups is independently selected from the group consisting of H, OH, NO2NH,, SH, CN, halogen, =O, C(=O)H, C(=O)CH 3, CO2H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstitued aryl; wherein R1, R2, R3 could form part of a heterocyclic ring; R2 can be independently an internal salt; wherein X1, X2 and X3 on formula (I) are independently placed in any particular position of the chain and independently selected of H, OH, OR', SH, SR', SOR', SO2R', NO2, NH2, NHR', N(R')2, NHC(O)R', CN, halogen, =O, C(=O)H, C(=O)CH3, CO,H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic; wherein substituent groups defined by R' are each independently selected from the group consisting of H, OH, OR', SH, SR', SOR', SO2R', NO, NH2, NHR', N(R')2, NHC(O)R', CN, halogen, =O, C(=O)H, C(=O)CH3, CO2H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic; wherein x can be between 6 and 20; and wherein the dotted line is one or several double bonds placed in any particular position of the side chain; are useful as antitumor compounds and include compound IK-8-73-4 of structure (a) which was isolated from a sponge Pachastrissa sp.

L'invention concerne des composés correspondant à la formule (I), dans laquelle les groupes de substitution définis par R¿1?, R¿2?, R¿3? et R¿4? sont sélectionnés, de manière indépendante, parmi H, C(=O)R', P(=O)R'R'', S(=O)R'R'', alkyle C¿1?-C¿18? substitué ou non substitué, alcényle C¿2?-C¿18? substitué ou non substitué, alkynyle C¿2?-C¿18? substitué ou non substitué, aryle substitué ou non substitué; dans lesquels chacun des groupes R' et R'' est choisi de manière indépendante parmi H, OH, NO¿2?, NH¿2?, SH, CN, halogène, =O, C(=O)H, C(=O)CH¿3?, CO¿2?H, CO¿2?CH¿3?, alkyle C¿1?-C¿18? substitué ou non substitué, alcényle C¿2?-C¿18? substitué ou non substitué, alkynyle C¿2?-C¿18? substitué ou non substitué, aryle substitué ou non substitué; où R¿1?, R¿2? et R¿3? pourraient faire partie d'un noyau hétérocyclique; R¿2? pouvant être, de manière indépendante, un sel interne; X¿1?, X¿2?, et X¿3? étant placés, dans la formule (I), de manière indépendante à n'importe quelle position de la chaîne et étant choisis parmi H, OH, OR', SH, SR', SOR', SO¿2?R', NO¿2?, NH¿2?, NHR', N(R')¿2?, NHC(O)R', CN, halogène, =O, C(=O)H, C(=O)CH¿3?, CO¿2?H, CO¿2?CH¿3?, alkyle C¿1?-C¿18? substitué ou non substitué, alcényle C¿2?-C¿18? substitué ou non substitué, alkynyle C¿2?-C¿18? substitué ou non substitué, aryle substitué ou non substitué, hétéroaromatique substitué ou non substitué; les groupes de substitution définis par R' étant choisis de manière indépendante parmi H, OH, OR', SH, SR', SOR', SO¿2?R', NO¿2?, NH¿2?, NHR', N(R')¿2?, NHC(O)R', CN, halogène, =O, C(=O)H, C(=O)CH¿3?, CO¿2?H, CO¿2?CH¿3?, alkyle C¿1?-C¿18? substitué ou non substitué, alcényle C¿2?-C¿18? substitué ou non substitué, alkynyle C¿2?-C¿18? substitué ou non substitué, aryle substitué ou non substitué, hétéroaromatique substitué ou non substitué; x étant compris entre 6 et 20; et la ligne en pointillés représentant au moins une double liaison placée à n'importe quelle position de la chaîne latérale. Ces composés sont utiles comme antitumoraux et contiennent le composé IK-8-73-4 ayant la structure (a), qui a été isolée chez l'éponge Pachastrissa sp.

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