IP Library Granted Patent US 7,056,953
Granted Patent B2
US 7,056,953 · App. 10/848,454 · Granted Jun 6, 2006

(E)-styryl sulfone anticancer agents

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Quick Facts
Patent No.
US 7,056,953
App. No.
10/848,454
Granted
Jun 6, 2006
Kind
B2
Abstract

(E)-styryl benzylsulfones of formula I are useful as anticancer agents: wherein R 1 , R 2 , R 3 , and R 4 are as defined herein.

Claims (16)

1. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of the formula:

wherein:

R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, fluoro, chloro, bromo, C1–C6 alkyl, C1–C6 alkoxy, nitro, cyano and trifluoromethyl,

with the proviso that:

(a) R 1 , R 2 , and R 3 may not all be hydrogen when R 4 is 2-chloro or 4-chloro;

(b) when R 1 and R 3 are hydrogen and R 2 is 4-bromo or 4-chloro, then R 4 may not be 4-chloro, 4-fluoro or 4-bromo;

(c) when R 1 and R 3 are hydrogen and R 2 is 4-fluoro, then R 4 may not be 4-fluoro or 4-bromo;

(d) when R 1 is hydrogen, and R 4 is 2-fluoro, then R 2 and R 3 may not be 4-fluoro; and

(e) when R 1 is hydrogen and R 3 is 4-hydrogen, 4-chloro, 4-bromo, 4-methyl or 4-methoxy, and R 4 is 2-hydrogen, 2-chloro, or 2-fluoro, then R 2 may not be 4-hydrogen, 4-chloro, 4-fluoro, or 4-bromo.

2. The composition according to claim 1 wherein the compound is selected from the group consisting of (E)-4-fluorostyryl-4-trifluoromethyl-benzylsulfone, (E)-2-trifluoromethyl-4-fluorostyryl-2,4-dichlorobenzyl-sulfone and (E)-4-fluorostyryl-4-cyanobenzylsulfone, (E)-4-fluorostyryl-3,4-dichlorobenzylsulfone, (E)-4-fluorostyryl-2,4-dichlorobenzylsulfone, (E)-2-chloro-4-fluorostyryl-4-chlorobenzylsulfone, and (E)-4-fluorostyryl-4-nitrobenzylsulfone, (E)-4-chlorostyryl-4-nitrobenzylsulfone, (E)-4-nitrostyryl-4-fluorobenzylsulfone, (E)-4-nitrostyryl-4-bromobenzylsulfone, (E)-4-nitrostyryl-4-cyanobenzylsulfone, (E)-4-fluorostyryl-4-methoxy-benzylsulfone, (E)-4-chlorostyryl-4-methoxybenzylsulfone, (E)-4-bromostyryl-4-methoxybenzylsulfone and (E)-4-nitrostyryl-4-methoxybenzylsulfone.

3. A method of treating an individual for cancer comprising administering an effective amount of a pharmaceutical composition according to claim 1 .

4. A method of treating an individual for cancer comprising administering an effective amount of a pharmaceutical composition according to claim 2 .

5. The method of according to claim 3 wherein the cancer is selected from the group consisting of ovarian, breast, prostate, lung, renal, colorectal and brain cancers.

6. The method of according to claim 4 wherein the cancer is selected from the group consisting of ovarian, breast, prostate, lung, renal, colorectal and brain cancers.

7. A method of inducing apoptosis of tumor cells in an individual afflicted with cancer comprising administering to said individual an effective amount of a pharmaceutical composition according to claim 1 .

8. The method according to claim 7 wherein the tumor cells are selected from the group consisting of ovarian, breast, prostate, lung, colorectal, renal and brain tumors.