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Metabolites of selective androgen receptor modulators and methods of use thereof

A technology of androgen receptors and metabolites, applied in the field of selective androgen receptor modulators, which can solve problems such as harm to individual health, increased susceptibility to infection, and susceptibility to damage

Inactive Publication Date: 2007-05-30
UNIV OF TENNESSEE RES FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, changes that occur during sarcoid wasting can result in a weakened physical condition that is detrimental to the individual's health, leading to increased susceptibility to infection, poor performance status, and susceptibility to injury

Method used

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  • Metabolites of selective androgen receptor modulators and methods of use thereof
  • Metabolites of selective androgen receptor modulators and methods of use thereof
  • Metabolites of selective androgen receptor modulators and methods of use thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0334] The preparation of pharmaceutical compositions containing active ingredients is known in the art, for example by mixing, granulating or tabletting methods. The active therapeutic ingredient is usually mixed with excipients which are pharmaceutically acceptable and compatible with the active ingredient. For oral administration, the SARM drugs or their physiologically tolerable derivatives such as salts, esters, N-oxides etc. are mixed with additives customary for this purpose such as excipients, stabilizers or inert diluents, and Conversion into a form suitable for administration, such as tablets, coated tablets, hard or soft gelatin capsules, aqueous, alcoholic or oily solutions, is carried out by conventional methods. For parenteral administration, the SARM drugs or their physiologically tolerable derivatives such as salts, esters, N-oxides, etc. are converted into solutions, suspensions or emulsions, if necessary, with conventionally used and suitable Substances of i...

Embodiment 1

[0342] Non-steroidal ligands with androgenic and anabolic activity

[0343] Some of the SARM compounds provided herein were designed and synthesized and evaluated for their in vitro and in vivo pharmacological activities. Study of androgen receptor binding affinity in vitro and ability to maintain androgen-dependent tissue growth in castrated animals. Androgenic activity is monitored by the ability of the SARM compound to maintain and / or stimulate the growth of the prostate and seminal vesicles, as measured by body weight. Anabolic activity is monitored as the ability of the SARM compound to maintain and / or stimulate growth of the levator ani muscle as measured by weight.

[0344] resolve resolution

[0345] (2R)-1-Methacryloylpyrrolidine-2-carboxylic acid (R-129). D-proline (R-128, 14.93 g, 0.13 mol) was dissolved in 71 mL of 2N NaOH, cooled on an ice bath, and the resulting basic solution was diluted with acetone (71 mL). A solution of methacryloyl chloride 127 (13.56 g,...

Embodiment 2

[0354] Non-steroidal ligands with androgenic and anabolic activity

[0355] The in vivo efficacy and acute toxicity of four new non-steroidal androgens (compounds III, IV, VI and VII) were tested in rats. In vitro assays confirm that these compounds bind the androgen receptor with very high affinity. The structures and names of the four compounds are shown below:

[0356]

[0357] Compound III R=F

[0358] Compound IV R=NHCOCH 3

[0359] Compound VI R=COCH 3

[0360] Compound VII R=COC 2 h 5

[0361] experimental method

[0362]Materials: S isomers of compounds III, IV, VI and VII and R isomers of compound III were synthesized according to the route shown in FIG. 9 . Testosterone propionate (TP), polyethylene glycol 300 (PEG300, reagent grade) and neutral buffered formalin (10% w / v) were purchased from Sigma Chemical Company (St Louis, MO). Alzet osmotic pumps (model 2002) were purchased from AlzaCorp. (Palo Alto, CA).

[0363] Animals: Juvenile male Sprague-Daw...

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Abstract

This invention provides metabolites of a class of androgen receptor targeting agents (ARTA). The SARM compounds and their metabolites, either alone or as a composition, 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, benign prostate hyperplasia, alterations in mood and cognition and prostate cancer; 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, endometriosis, breast cancer, uterine cancer and ovarian cancer; d) treatment and / or prevention of acute and / or chronic muscular wasting conditions; e) preventing and / or treating dry eye conditions; f) oral androgen replacement therapy; g) decreasing the incidence of, halting or causing a regression of prostate cancer; and / or h) inducing apoptosis in a cancer cell.

Description

field of invention [0001] The present invention relates to a new class of metabolites of androgen receptor targeting active agents (ARTAs) which are selective androgen receptor modulators (SARMs). Said SARM compounds and their metabolites are useful in a) male contraception; b) in the treatment of various hormone-related disorders, such as those associated with decreased androgen in aging males (ADAM), such as fatigue, depression, decreased libido, sexual dysfunction , erectile dysfunction, hypogonadism, osteoporosis, alopecia, anemia, obesity, sarcopenia, osteopenia, osteoporosis, benign prostatic hyperplasia, mood and cognitive changes, and prostate cancer; c) treatment with female androgen Reduced (ADIF)-related conditions such as sexual dysfunction, decreased libido, hypogonadism, sarcopenia, osteopenia, osteoporosis, cognitive and mood changes, depression, anemia, hair loss, obesity, endometriosis d) treatment and / or prevention of acute and / or chronic muscle wasting; e) ...

Claims

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Application Information

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IPC IPC(8): A61K31/275C07G3/00C07C233/05A61K31/70C07C233/87C07C235/24C07C255/49C07F7/22
CPCA61K31/7036A61K31/166C07H15/18C07C235/24C07H15/203A61P13/08A61P15/12A61P15/16A61P35/00A61P43/00
Inventor 詹姆斯·T·多尔顿杜安·D·米勒尹冬华何雅丽
Owner UNIV OF TENNESSEE RES FOUND
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