Antiandrogenic biphenyls
AssigneeEndorecherche, Inc.
InventorsFernand Labrie, Shankar Mohan Singh, Van Luu-The
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Abstract
Biphenyl derivatives are disclosed for use in the treatment of androgen-dependent diseases such as prostate cancer, benign prostatic hyperplasia, precicious puberty, polycystic ovarian syndrome, acne, hirsutism, seborrhea, androgenic alopecia and premature male baldness. For example, some preferred compounds having the structure: 1 are formulated together with pharmaceutically acceptable diluent or carrier for topical use in the treatment of androgen-dependent prostate cancer.
Claims45
An antiandrogenic compound of the molecular formula:
- 150
- Wherein R2, R3, R5 and R6 are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide, C1-C3 alkyl, C1-C3 fluoroalkyl, nitro, carboxamide,
- 151
- and
- 152
- (Ra being C1-C3 alkyl);
- Wherein R4 and R4′ are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide,
- 153
- (Ra being C1-C3 alkyl), —ORb, —PO(ORb)2, —c≡C—Rb, (Rb being C1-C6 alkyl), C2-C3 trifluorohydroxyalkyl, trifluoromethyl, nitro, amine, acetylamine, sulphamine, and ureide;
- Wherein at least one of R4 and R4′ is not hydrogen;
- Wherein R2′ and R6′ are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide, trifluoromethyl, nitro, carboxamide,
- 154
- and
- 155
- (Ra being C1-C3 alkyl);
- Wherein R3′ and R5′ are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide, C2-C3 trifluorohydroxyalkyl, C1-C3 alkyl, C1-C3 fluoroalkyl, nitro, and carboxamide.
A pharmaceutical composition comprising a pharmaceutically acceptable diluent or carrier and a therapeutically effective amount of at least one antiandrogenic compound of the molecular formula:
- 163
- Wherein R2, R3, R5 and R6 are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide, C1-C3 alkyl C1-C3 fluoroalkyl, nitro, carboxamide,
- 164
- and
- 165
- (Ra being C1-C3 alkyl);
- Wherein R4 and R4′are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide,
- 166
- (Ra being C1-C3 alkyl), —ORb, —PO(ORb)2′—C≡C—Rb , (Rb being C1-C6 alkyl), C2-C3 trifluorohydroxyalkyl, trifluoromethyl, nitro, amine, acetylamine, sulphamine, and ureide;
- Wherein at least one of R4 and R4′ is not hydrogen;
- Wherein R2′ and R6′ are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide, trifluoromethyl, nitro, carboxamide,
- 167
- (Ra being C1-C3 alkyl);
- Wherein R3′ and R5′ are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide, C2-C3 trifluorohydroxyalkyl, C1-C3 alkyl, C1-C3 fluoroalkyl, nitro, and carboxamide;
The pharmaceutical composition of claim 11 having the following molecular structure:
- 174
- 3-chloro-2′,6′-difluoro-biphenyl-4-carbonitrile
An antiandrogenic compound of the molecular formula:
- 175
- Wherein R2, R3, R5 and R6 are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide, C1-C3 alkyl, C1-C3 polyfluoroalkyl, nitro, and carboxamide,
- 176
- and
- 177
- (Ra being C1-C3alkyl);
- Wherein R4 and R4′ are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide,
- 178
- Ra, and
- 179
- (Ra being C1-3 alkyl), —ORb, —PO(ORb)2, —C≡C—Rb, (Rb being C1-C6 alkyl), C2-C3 trifluorohydroxyalkyl, trifluoromethyl, nitro, amine, acetylamine, sulphamine, and ureide;
- Wherein at least one of R4 and R4′ is not hydrogen;
- Wherein R2′and R6′ are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide, trifluoromethyl, nitro, carboxamide,
- 180
- and
- 181
- (Ra being C1-C3-alkyl);
- Wherein R3′ and R5′ are independently selected from the group consisting of hydrogen, fluoride, chloride, bromide, iodide, cyanide, C2-C3 trifluorohydroxyalkyl, C1-C3 alkyl, C1-C3 polyfluoroalkyl, nitro, and carboxamide.
The antiandrogenic compound having the following molecular structure:
- 182
Dependencies are inferred from the claim text.