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CRYSTALLINE FORMS OF 3β -HYDROXYANDROST-5-EN-17-ONE

IP.com Disclosure Number: IPCOM000250386D
Publication Date: 2017-Jul-09
Document File: 6 page(s) / 459K

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The IP.com Prior Art Database

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CRYSTALLINE FORMS OF 3β -HYDROXYANDROST-5-EN-17-ONE

Described herein are crystalline forms of 3β -hydroxyandrost-5-en-17-one, referred

herein as compound A.

Samples of the crystalline forms of Compound A were prepared according to the

processes described in examples 1 to 4 below, and were analyzed by X-ray powder diffraction

("XRPD"). Figures 1-4 present the XRPD patterns of the obtained forms of Compound A.

Figure 1: XRPD pattern of crystalline form of Compound A prepared by example 1:

Full peak list:

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

8.1 10.97 45.0

15.0 5.91 68.6

15.1 5.85 100.0

15.5 5.70 61.4

15.8 5.61 4.1

16.0 5.53 31.1

16.8 5.27 10.0

17.7 5.00 51.5

17.9 4.97 38.1

18.0 4.92 28.0

18.2 4.87 36.7

18.7 4.74 44.0

19.2 4.63 8.1

19.5 4.56 12.4

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

20.0 4.43 7.8

20.2 4.39 6.5

20.4 4.36 10.3

23.9 3.73 4.1

24.1 3.69 6.9

24.8 3.59 3.2

25.1 3.55 7.0

25.3 3.51 3.1

26.7 3.33 5.3

26.9 3.31 3.5

29.4 3.03 65.7

29.5 3.03 58.1

30.1 2.97 4.7

30.3 2.95 5.0

5 10 15 20 25 30 35 40 2Theta (°)

0

500

1000

1500

2000

2500

3000

In te

n s it y (

c p

s )

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

31.5 2.84 4.8

31.6 2.83 6.2

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

38.9 2.32 2.7

Figure 2: XRPD pattern of crystalline form of Compound A prepared by example 2:

Full peak list:

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

7.8 11.39 12.3

11.0 8.04 32.1

12.3 7.17 39.1

14.1 6.30 38.6

15.1 5.88 16.9

15.6 5.69 87.8

15.7 5.63 24.2

16.1 5.49 100.0

17.4 5.09 5.4

17.9 4.97 33.3

19.1 4.64 21.3

19.4 4.57 21.0

19.5 4.54 32.2

19.9 4.46 31.3

20.0 4.44 41.8

21.0 4.22 19.9

21.7 4.09 5.7

22.8 3.89 16.0

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

23.3 3.81 8.0

23.5 3.79 16.2

23.8 3.74 14.5

23.9 3.72 7.1

24.6 3.61 5.4

24.8 3.59 13.6

26.3 3.39 7.8

26.4 3.38 9.0

26.5 3.37 6.7

27.6 3.23 9.0

27.7 3.22 12.6

28.0 3.18 8.4

28.3 3.15 12.4

28.8 3.10 7.9

31.7 2.82 7.4

33.5 2.67 5.2

35.3 2.54 8.9

37.2 2.41 5.6

5 10 15 20 25 30 35 40 2Theta (°)

0

100

200

300

400

500

600

In te

n s it y (

c p

s )

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

37.4 2.41 9.9

37.4 2.41 8.0

38.4 2.34 5.4

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

38.9 2.31 5.8

39.1 2.30 5.3

Figure 3: XRPD pattern of crystalline form of Compound A prepared by example 3:

Full peak list:

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

7.9 11.24 7.0

8.3 10.64 2.4

9.1 9.75 3.4

11.5 7.68 3.0

13.7 6.44 9.5

14.1 6.29 12.8

14.4 6.17 3.9

14.6 6.06 12.8

14.7 6.01 16.6

15.0 5.91 11.8

15.5 5.71 100.0

15.7 5.63 34.1

16.0 5.55 10.5

16.1 5.50 4.9

17.2 5.16 13.6

17.3 5.12 19.5

17.7 5.01 13.4

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

18.1 4.90 9.0

18.6 4.76 5.2

19.5 4.56 5.6

19.7 4.51 5.3

19.9 4.47 4.4

20.7 4.29 11.8

20.9 4.24 3.8

21.8 4.07 4.9

21.9 4.05 6.1

22.7 3.91 2.1

23.3 3.81 3.2

23.5 3.79 2.7

23.9 3.73 3.1

24.5 3.64 2.3

25.1 3.55 3.6

27.0 3.30 4.9

29.4 3.04 2.6

5 10 15 20 25 30 35 40 2Theta (°)

0

500

1000

1500

In te

n s it y (

c p

s )

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

31.8 2.81 3.5

32.0 2.80 2.9

Pos.

[°2θ]

d-spacing

[Å]

Rel. Int.

[%]

32.2 2.78 2.1

Fig...