LARGE-SCALE SYNTHESIS OF SELECTIVE ANDROGEN RECEPTOR MODULATORS

Title:

LARGE-SCALE SYNTHESIS OF SELECTIVE ANDROGEN RECEPTOR MODULATORS

Document Type and Number:

WIPO Patent Application WO2004062612

Kind Code:

A3

Abstract:

The present invention relates to a synthetic process for the preparation of a novel class of androgen receptor targeting agents (ARTA) which demonstrate androgenic and anabolic activity of a nonsteroidal ligand for the androgen receptor. The agents define a new subclass of compounds which are selective androgen receptor modulators (SARM) which are useful for a) male contraception; b) treatment of a variety of hormone-related conditions, for example conditions associated with Androgen Decline in Aging Male (ADAM), such as fatigue, depression, decreased libido, sexual dysfunction, erectile dysfunction, hypogonadism, osteoporosis, hair loss, anemia, obesity, sarcopenia, osteopenia, osteoporosis, and alterations in mood and cognition; c) treatment of conditions associated with Androgen Decline in Female (ADIF), such as sexual dysfunction, decreased sexual libido, hypogonadism, sarcopenia, osteopenia, osteoporosis, alterations in cognition and mood, depression, anemia, hair loss, obesity and endometriosis, d) treatment and/or prevention of chronic muscular wasting; e) decreasing the incidence of, halting or causing a regression of prostate cancer; f) oral androgen replacement; g) preventing and/or treating dry eye conditions; h) treatment and/or prevention of begnin prostate hyperplasia (BPH); I) inducing apoptosis in a cancer cell; j) treatment and/or prevention of cancers of female sexual organs such as breast cancer, uterine cancer and ovarian cancer; and/or other clinical therapeutic and/or diagnostic areas. The process of the present invention is suitable for large-scale preparation, since all of the steps give rise to highly pure compounds, thus avoiding complicated purification procedures which ultimately lower the yield. Thus the present invention provides methods for the synthesis of non-steroidal agonist compounds, that can be used for industrial large-scale synthesis, and that provide highly pure products in high yield.

Inventors:

STEINER MITCHELL S (US)
CHUNG KIWON (US)
DALTON JAMES (US)
MILLER DUANE D (US)
VEVERKA KAREN A (US)

Application Number:

PCT/US2004/000618

Publication Date:

November 04, 2004

Filing Date:

January 12, 2004

Export Citation:

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Assignee:

GTX INC (US)
STEINER MITCHELL S (US)
CHUNG KIWON (US)
DALTON JAMES (US)
MILLER DUANE D (US)
VEVERKA KAREN A (US)

International Classes:

C07C231/12; C07C235/24; (IPC1-7): C07C231/12; C07C231/00

Foreign References:

US6482861B2	2002-11-19
US6071957A	2000-06-06

Other References: