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Synthetic and crystalline forms of intermediates of 3ß-acetoxy-17-(3-pyridyl)androsta-5,16-diene

IP.com Disclosure Number: IPCOM000234931D
Publication Date: 2014-Feb-17
Document File: 3 page(s) / 79K

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Page 01 of 3

Synthetic and crystalline forms of intermediates of 3ß-acetoxy-17-(3-pyridyl)androsta-

5,16-diene

    Dehyroepiandrosterone-3-acetate (referred to as compound 1) of the following formula:

O

AcO

Compound 1

and 3ß-acetoxy-17-(3-pyridyl)androsta-5,16-diene sulfate salt (referred to as Compound 2) of the following formula:

AcO

N

H2SO4

Compound 2

are intermediates in the synthesis of 3ß-acetoxy-17-(3-pyridyl)androsta-5,16-diene (referred to as Compound A) of the following formula:

                     Compound A
The synthesis and solid state forms of Compound 1 and Compound 2 are disclosed

hereinafter.


Page 02 of 3

Crystalline Compound 1

    The starting material Dehyroepiandrosterone-3-acetate (Compound 1) can be prepared according to processes that are known in art (e.g. European Journal of Medicinal Chemistry 2013, 66, 171). Compound 1 was dissolved in acetone (4 -6 volumes) and a solution was formed. Water (4 -6 volumes) was added and precipitation occurred. The material was isolated by filtration and dried at 60ºC under vacuum, for 10 hours, affording a crystalline form of dehyroepiandrosterone-3-acetate.

The product was analyzed by PXRD and the pattern is depicted in Figure 1.

Figure 1: PXRD pattern of crystalline Compound 1:

Main peaks: 8.9, 10.8, 12.9, 13.2, 14.5, 16.1, 17.1, 18.9, 19.5, 20.2, 21.4, 23.7 and 23.9 ± 0.2 degrees 2Ө.

Crystalline Compound 2

    The starting material Compound A can be prepared according to processes that are known in art (e.g. US patent 5604213). Compound A...