US 6,645,998 B2 · Tocopherols, tocotrienols, other chroman and side chain derivatives and uses thereof

Abstract

The present invention provides an antiproliferative compound having the structural formula wherein X is oxygen, nitrogen or sulfur; R1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxylic acid, carboxylate, carboxamide, ester, thioamide, thiolacid, thiolester, saccharide, alkoxy-linked saccharide, amine, sulfonate, sulfate, phosphate, alcohol, ethers and nitriles; R2 is hydrogen, methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide and amine; R3 is selected from the group consisting of hydrogen, methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide and amine; R4 is of methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide and amine; and R5 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxyl, amide and ester. Also provided is a method for inducing apoptosis in a cell comprising administering a composition comprising a compound.

Claims16

Dependent claims

A method for the treatment of a cell proliferative disease comprising administering to an animal a pharmacologically effective dose of a compound having a structural formula:

wherein X is oxygen;
R1 is —C1-10 alkylene-COOH —C1-4 alkylene-CONH2, —C1-4 alkylene-COO—C1-4 alkyl, —C1-4 alkylene-CON(C1-4 alkylene-COOH)2, C1-4 alkylene-OH, C1-4alkylene-NH3-halo, or C1-4 alkylene-OSO2NH(C1-4 alkyl)3;
R2, R3 are H or C1-4 alkyl;
R4 is C1-4 alkyl;
and
R5 is methyl, C7-17 alkyl, COOH, C7-17 olefinic group containing 3 to 5 ethylenic bonds, —C═C—COO—C1-4 alkyl or C1-4 alkylene-COO—C1-4 alkyl with the proviso that R1 cannot be —C2-4 alkylene-COOH when R2, R3, and R4 are methyl, and R5 is a C16 alkyl;
or a pharmaceutical composition thereof.

4 more elements

A method of inducing apoptosis of a cell, comprising the step of contacting said cell with a pharmacologically effective dose of a compound having a structural formula:

wherein X is oxygen;
R1 is —C1-10 alkylene-COOH —C1-4 alkylene-CONH2, —C1-4 alkylene-COO—C1-4 alkyl, —C1-4 alkylene-CON(C1-4 alkylene-COOH)2, C1-4 alkylene-OH, C1-4 alkylene-NH3-halo, or C1-4 alkylene-OSO2NH(C1-4 alkyl)3;
R2, R3 are H or C1-4 alkyl;
R4 is C1-4 alkyl;
and
R5 is methyl, C7-17 alkyl, COOH, C7-17 olefinic group containing 3 to 5 ethylenic bonds, —C═C—COO—C1-4 alkyl or C1-4 alkylene-COO—C1-4 alkyl with the proviso that R1 cannot be —C2-4 alkylene-COOH when R2, R3, and R4 are methyl, and R5 is a C16 alkyl;
or a pharmaceutical composition thereof.

4 more elements

Dependencies are inferred from the claim text.

Tocopherols, tocotrienols, other chroman and side chain derivatives and uses thereof

Life of this patent

Tocopherols, tocotrienols, other chroman and side chain derivatives and uses thereof

Life of this patent

Abstract

Claims16