US 2008/0194659 A1Published application

Cinnamic, Phenylpropiolic and Phenylpropanoic Acid Derivatives Useful as Anti-Tumor Agents

AssigneeSigma-Tau Farmaceutiche Riunite S.p.A.

InventorsClaudio Pisano, Gianfranco Battistuzzi, Maria Di Marzo, Giuseppe Giannini, Mauro Marzi, Loredana Vesci, Franco Zunino, Ricaardo Pezzi

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Abstract

Cinnamic and phenylpropiolic acid derivatives of formula (I) having antitumour and chemo sensitizing activity are described. Also described are pharmaceutical compositions containing the above-mentioned compounds, for the treatment of tumours.

Claims23

Dependent claims

A compound having the following formula I:

wherein:
n is either 0 or 1;
when n is 0, A is a monovalent group and is selected from the group consisting of:
OH, NH-OG, the group
where G and G′ are the same or different and are H, glycosyl or acetyl;
when n is 1, A is a divalent group selected from the group consisting of:
NH—S—S—NH and CH2—S—S—CH2;
Y is a group selected among HC═CH, FC═CF, FC═CH, CH═CF, CH2—CH2 and C—C;
R is the group:
where X is either O, NH;
R is the group:
Z selected from the group consisting of:
H;
(C6-C12) aryl or (C6-C12) aryl substituted with nitro, halogen, (C1-C4) alkoxycarbonyl, hydroxyl or amino;
(C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl;
(C6-C12) aryl-(CH2)n′, where aryl is substituted with nitro halogen, (C1-C4) alkoxycarbonyl, hydroxyl or amino;
where n′=0−3;
(C6-C12) aryl-CO, where aryl is substituted with nitro halogen (C1-C4) alkoxycarbonyl, hydroxy, amino;
and
(C3-C6) heterocyclyl-(C1-C4) alkyl where at least one of the CH2 of the heterocycle is substituted by O, S, NH;
R1 is selected from the group consisting of:
H;
NH2,
(C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl;
NH—(C2-C4) alkynyl;
NO2;
(C2-C4) alkynyl;
halogen;
(C6-C12) aryl;
(C6-C12) aryl-(C2-C4) alkynylene;
and
(C3-C6) heterocyclyl-(C2-C4) alkynylene where at least one of the CH2 of the heterocycle is substituted by O, S, NH;
R and R1, taken together with the aromatic group, form a polycyclic group having the following formula:
R2 is selected from the group consisting of:
H;
(C6-C12) aryl or (C6-C12) aryl substituted with nitro, halogen, (C1-C4) alkoxycarbonyl, hydroxyl or amino;
(C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl;
(C6-C12) aryl-(CH2)n—, where aryl is substituted with nitro halogen, (C1-C4) alkoxycarbonyl, hydroxyl or amino, where n″=0−3;
(C6-C12) aryl-CO, where aryl is substituted with nitro halogen (C1-C4);
alkoxycarbonyl, hydroxy, amino;
and
(C3-C6) heterocyclyl-(C1-C3) alkylene where at least one of the CH2 of the heterocycle is substituted by O, S, NH;
R3 is selected from the group consisting of:
H;
(C1-C4) alkyl, (C2-C4) alkenyl;
(C1-C4) alkyl —NH;
(C1-C4)-alkyl-(C3-C6)-heterocyclylene, where at least one of the CH2 of the heterocycle is substituted by O, S, NH;
(C6-C12)aryl;
and
(C3-C6) heteroaryl where at least one of the CH of the heterocycle is substituted by O, S, NH;
R4 is selected from the group consisting of:
H;
(C1-C4) alkyl;
(C6-C12) aryl;
(C6-C12) aryl-(C1-C4) alkynylene;
(C2-C4) alkanoyl;
and
—(C6-C12) aryl-CO;
R5 is selected from the group consisting of:
H;
linear or branched (C1-C4) alkyl;
linear or branched (C2-C4) alkenyl;
and
OR6, where R6 is H, (C1-C4) alkyl mesyl, tosyl, (C1-C4)alkanoyl.

61 more elements

Dependencies are inferred from the claim text.

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