Ester and ether derivatives of 4-hydroxy...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Cyclopentanohydrophenanthrene ring system doai

Reexamination Certificate

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Reexamination Certificate

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06586417

ABSTRACT:

BACKGROUND OF INVENTION
This invention relates to the ester and ether derivatives of 4-hydroxy 4-androstenedione as a means of regulating athletic function in humans. In men, the normal balance of sex steroids is characterized by a greater amount of androgens over estrogens. When estrogen exceeds androgen levels in males a cascade of detrimental effects can take place for instance, decreased sperm count, low free testosterone levels, decreased muscle mass and decreased strength. When androgens are manipulated to exceed estrogen above the normal androgen to estrogen ratio the exact opposite takes place with an emphasis on the promotion of lean body mass and strength to aid in enhancing physical performance.
The use of 4-hydroxy 4-androstenedione is intended to gradually increase androgen levels while simultaneously decreasing estrogen and dihydrotestosterone (DHT). Natural androgen production is increased by the stimulation of the hypothalamic pituitary axis via an increase in luteinizing hormone (LH) levels coupled by the direct stimulation of testosterone by 4-hydroxy 4-androstenedione. Luteinizing hormone (LH) is responsible for the production of total serum testosterone and testicular function. This gradual increase in testosterone then decreases the amount of steroid hormone binding globulin (SHBG) which increases the amount of free or active testosterone. Testosterone and dihydrotestosterone (DHT) circulate in plasma either unbound (free approximately 2-3%) or bound to plasma proteins. The binding proteins include sex hormone-binding globulin (SHBG) and albumin. SHBG is a &bgr;-globulin that has a low capacity for steroids, but binds with high affinity. SHBG has its highest affinity for DHT and its lowest affinity for estradiol. In men, circulating testosterone is bound 44-65% to SHBG and 33-54% to albumin, whereas in women, testosterone is bound 66-78% to SHBG and 20-32% to albumin.
Serious and/or professional athletes are known to utilize intramuscular injection and/or peroral administration of pharmaceutical androgens for the promotion of muscle mass and athletic performance. Various testosterone esters in oil depot form have been utilized as intramuscular injection. These weekly injections of synthetic testosterone cause supraphysiological surges in androgen levels which then leave the body deficient in androgens until the next injection. These supraphysiological levels of testosterones readily convert to estrogen and dihydrotestosterone (DHT) which can lead to side effects such as gynocomastia and benign prostrate hypertrophy (BPH). Another negative side effect is the possible down regulation of the hypothalamic pituitary axis resulting in loss of natural testosterone production.
The oral route of synthetic androgen administration consists of testosterone derivatives that are 17 alpha-alkylated for enhanced oral bioavailability (i.e. Methyltestosterone). This alkylation allows the steroids to withstand the 17 beta-hydroxyl oxidation in the liver. This appears to alleviate the dosing and blood hormone problems as compared to injections but it can cause undue stress to the liver and increase the possibility of hepatotoxicity.
Pharmaceutical anti-estrogens have also been utilized in an attempt to promote androgen accumulation. Theoretically the inhibition of estrogen absorption should shift the hormonal balance toward a predominant androgen ratio. Although this method of therapy is inadequate due to the mechanism of action that most anti-estrogens are based upon. Anti-estrogen drugs such as Tamoxifen act on the estrogen receptor and thus block or inhibit estrogen absorption. This receptor blockade inhibits absorption but it does not lower total circulating estrogen levels. These anti-estrogens also do not dictate the specific site of estrogen receptor inhibition in the body. Since the actual estrogen concentration has not decreased there is no signal sent to the hypothalamic-pituitary axis to increase androgen production.
U.S. Pat. No. 5,880,117 to Patrick Arnold, relates a method of using of using the oral precursor hormone 4-androstenediol as a means of increasing testosterone levels in humans. This hormone represents an improvement in standard therapies, since 4-androstenediol does not seem to be open to aromatase in its initial state. The possibility that this compound will convert to an estrogen over an androgen is chemically unlikely. The end product testosterone however is still readily aromatized. The compound suggested in this patent does offer advantages over standard therapies in that the compound in question avoids a direct path of estrogen conversion and provides a less toxic peroral route of administration. The target hormone of replacement may still be less than ideal due to it's conversion to estrogen and dihydrotestosterone (DHT).
U.S. Pat. No. 6,242,436 to William Llewellyn, relates a method of using the oral precursor hormones 5alpha-androstanediol or 5alpha-androstanedione as a means of increasing dihydrotestosterone levels in humans. Dihydrotestosterone (DHT) is a more potent form of testosterone, shown to be roughly three to four times more active in the human body in comparison. This hormone represents an improvement, since 5alpha-androstanediol or 5alpha-androstanedione are natural, non-toxic, and quickly metabolized to active form after oral administration and unable to be aromatized into estrogens due to their structure. The compound suggested in this patent does offer advantages over standard therapies in that the compound in question avoids a direct path of estrogen conversion and provides a less toxic peroral route of administration. However, dihydrotestosterone (DHT) is not the most ideal form of testosterone due to it's causative relationship with benign prostrate hypertrophy (BPH) and other androgenic side effects.
U.S. Pat. No. 5,861,389 to Radlmaier, et al. discloses a method of increasing androgen levels in males by administering various aromatase inhibitors including atamestane, formestane, pentrozole, arimidex, fadrozole, and vorozole. These compounds block the aromatase enzyme which is responsible for the conversion of androgen to estrogens. Long term studies with aromatase inhibitor atamestane clearly demonstrates the restoration of androgens over estrogens at 24 and 48 weeks respectively. The method of this invention dictates the gradual decrease in estrogen blood concentration, which produces a signal to increase natural androgen production. This hormonal signal results in increased total and free androgen concentrations. This invention is an improvement over the standard exogenous administration of synthetic androgens for male androgen deficiency. These improvements include an inability to shut down the hypothalamic-pituitary axis, provide a safer oral route and not cause a supraphysiological surge in androgen concentrations.
SUMMARY OF INVENTION
The use of illicit synthetic exogenous testosterone for the promotion of muscle mass and work performance is well known throughout athletic circles. However these therapies, besides being illegal, result in the aromatization of the target hormone and put undue stress upon the liver. Dietary supplement manufactures have attempted to correct these problems by the use of pro-hormones for the promotion of physical performance. For instance, U.S. Pat. Nos. 5,880,117 and 6,242,436 attempt to correct some of these problems by the peroral administration of androgen precursors. Now while the active androgen precursor is unable to aromatize, the target hormone of U.S. Pat. No. 5,880,117 can produce substantial conversion to estrogen and dihydrotestosterone (DHT) while the target hormone of U.S. Pat. No. 6,242,436 is directly converted to dihydrotestosterone (DHT). The problem of the present invention is to provide a compound that gradually increases androgen levels for the promotion of fat free mass and athletic performance without causing aromatization, hepatotoxicity, or supraphysiological surges in androgen blood concentrations. According to the invention these problems are solved b

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