Substituted organosulfur compounds and methods of using thereof
AssigneeACEA Biosciences, Inc.
InventorsXiao Xu, Haoyun An, Xiaobo Wang
Life of this patent
Estimating the term…
Abstract
The present invention provides substituted di-, tri-, tetra- and penta-sulfide compounds and compositions, and methods of using the same for the treatment and/or prevention of a cell proliferative disorder. The present invention also provides methods for preparing trisulfide compounds and compositions.
Claims29
A compound having the formula:
- wherein A and B are the same, and are optionally substituted phenyl rings;
- each S is optionally in the form of an oxide;
- each R is H, halogen, carboxyl, cyano, amino, amido, SR1, OR1 or R1, wherein each R1 is alkyl, alkenyl, alkynyl, aryl, or a carbocyclic ring, each of which is optionally substituted;
- p is 1;
- each n is independently 0-3;
- and
- wherein A and B together may form a cyclic ring system, and the optional substituents on each A and B are independently selected from the group consisting of F, Br, I, carboxyl, cyano, amino, amido, SR1, OR1 or R1, wherein each R1 is ethyl, propyl, isopropyl, butyl, sec-butyl, tertiary butyl, pentyl, hexyl, alkenyl, alkynyl, aryl, heteroaryl, a carbocyclic ring or a heterocyclic ring, each of which is optionally substituted and may contain a heteroatom;
- or R1 is alkyl that is substituted;
- and a pharmaceutically acceptable salt, ester, prodrug or metabolite thereof;
- provided said compound is not dibenzyltrisulfide, di(p-chlorobenzyl)trisulfide, (p-chlorobenzyl)benzyltrisulfide, di(p-nitrobenzyl)trisulfide, di(3-phenyl-2-propenyl)-trisulfide, diphenyltrisulfide, or di(p-t-butylphenyl)trisulfide.
A method for treating a cancer selected from the group consisting of sarcoma, epidermoid cancer, fibrosarcoma, leukemia, cervical cancer, lymphoma, lung cancer, colon cancer, CNS cancer, melanoma, ovarian cancer, renal cancer, prostate cancer, breast cancer, head and neck cancer, or pancreatic cancer, said method comprising administering to a system or a subject in need thereof an effective amount of the compound having the formula:
- wherein A and B are the same or different, and are independently an optionally substituted phenyl ring;
- each S is optionally in the form of an oxide;
- S1 and S2 are independently S, SO or SO2;
- each R is H, halogen, carboxyl, cyano, amino, amido, SR1, OR1 or R1, wherein each R1 is alkyl, alkenyl, alkynyl, aryl or a carbocyclic ring, each of which is optionally substituted;
- m, n and p are independently 0-3;
- wherein A and B together may form a cyclic ring system, and the optional substituents on each A and B are independently selected from the group consisting of F, Br, I, carboxyl, cyano, amino, amido, SR1, OR1 or R1, wherein each R1 is ethyl, propyl, isopropyl, butyl, sec-butyl, tertiary butyl, pentyl, hexyl, alkenyl, alkynyl, aryl, heteroaryl, a carbocyclic ring or a heterocyclic ring, each of which is optionally substituted and may contain a heteroatom;
- or R1 is alkyl that is substituted;
- or a pharmaceutical composition thereof;
- wherein said subject is human.
A pharmaceutical composition, comprising a compound having formula:
- wherein A and B are the same or different, and are independently an optionally substituted phenyl ring;
- each S is optionally in the form of an oxide;
- S1 and S2 are independently S, SO or SO2;
- each R is H, halogen, carboxyl, cyano, amino, amido, SR1, OR1 or R1, wherein each R1 is alkyl, alkenyl, alkynyl, aryl or a carbocyclic ring, each of which is optionally substituted;
- m, n and p are independently 0-3;
- wherein A and B together may form a cyclic ring system, and the optional substituents on each A and B are independently selected from the group consisting of halogen, carboxyl, cyano, amino, amido, SR1, OR1 or R1, wherein each R1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, a carbocyclic ring or a heterocyclic ring, each of which is optionally substituted and may contain a heteroatom;
- and a pharmaceutically acceptable excipient.
A compound having the formula:
- wherein A and B are different, and are independently an optionally substituted phenyl;
- each S is optionally in the form of an oxide;
- S1 and S2 are independently S, SO or SO2;
- each R is H, halogen, carboxyl, cyano, amino, amido, SR1, OR1 or R1, wherein each R1 is alkyl, alkenyl, alkynyl, aryl, or a carbocyclic ring, each of which is optionally substituted;
- m, n and p are independently 0-3;
- wherein A and B together may form a cyclic ring system, and the optional substituents on each A and B are independently selected from the group consisting of halogen, carboxyl, cyano, amino, amido, SR1, OR1 or R1, wherein each R1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, a carbocyclic ring or a heterocyclic ring, each of which is optionally substituted and may contain a heteroatom;
- and a pharmaceutically acceptable salt, ester, prodrug or metabolite thereof;
- provided said compound is not (p-chlorobenzyl)benzyltrisulfide.
Dependencies are inferred from the claim text.