METHOD OF MAKING AND USING 7alpha,11beta-DIMETHYL-17beta-HYDROXYESTR-4-EN-3-ONE 17-UNDECANOATE

Abstract

Methods of using 7α,11β-dimethyl-17β-hydroxy-4-estren-3-one bucyclate (I) and 7α,11β-dimethyl-17β-hydroxyestr-4-en-3-one 17-undecanoate (II)for various hormonal therapies, dosage forms comprising 7α,11β-dimethyl-17β-hydroxy-4-estren-3-one bucyclate and 7α,11β-dimethyl-17β-hydroxyestr-4-en-3-one 17-undecanoate, and processes for their preparation.

Description

CROSS-REFERENCE TO RELATED PATENT APPLICATIONS[0001]This application is a continuation of co-pending U.S. patent application Ser. No. 11 / 040,964, filed Jan. 21, 2005, which is a continuation of U.S. patent application Ser. No. 10 / 260,854, filed Sep. 30, 2002, which is a continuation of International Application No. PCT / US01 / 10293, filed Mar. 30, 2001, claiming the benefit of U.S. Provisional Patent Application No. 60 / 193,530, filed Mar. 30, 2000 and 60 / 194,440, filed Apr. 4, 2000. The disclosures of the '964 application, the '854 application, the '293 application, the '530 application and the '440 application are incorporated herein by reference.FIELD OF THE INVENTION[0002]The present invention generally relates to methods of making and using esters of androgenic steroids.BACKGROUND OF THE INVENTION[0003]Androgen is a term used to identify the human male sex hormones. These hormones, which are chemically classified as steroids, are produced in the body by the testis, the cortex of t...

AI Technical Summary

Benefits of technology

[0016]Another aspect of the present invention includes separate processes for preparing the bucyclate and undecanoate, which provide these actives in relatively high yield, and advantageously in a solid form, preferably crystalline, at room temperature. As both can be produced in solid form, the preparation of aqueous microcrystalline suspensions for parenteral administration is possible. Moreover, because these actives are solid at room temperature, one is able to control the average particle size and particle size distribution of the solids, thereby positively affecting the duration of activity after parenteral administration of the respective suspensions.

Problems solved by technology

In practice, however, this therapy can be problematic.

While parenteral administration is possible, it is impractical because testosterone remains active in the body for only a short time.

Unfortunately, the activity of these androgen esters is unpredictable.

Different androgens sharing the same ester group exhibit varying and unpredictable levels of activity, as do androgens having the same basic chemical structure, but different ester groups.

One drawback of this active is that it is not exceptionally long-acting—it must be administered IM every two weeks to maintain testosterone levels within a normal (therapeutic) range in hypogonadal men.

The development of androgens that exhibit activity after oral administration has been less successful.

However, this active cannot be administered on a long-term basis, as is required in androgen replacement therapy, because of its associated liver toxicity.

It is well known that androgens alkylated at the C17 position, such as methyltestosterone, exhibit such toxicity.

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