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Solid state forms of (S)-2-(2-(benzofuran-6-carbonyl)-5,7- dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3- (methylsulfonyl)phenyl) propanoic acid

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Publication Date: 2017-Jul-26
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Solid state forms of (S)-2-(2-(benzofuran-6-carbonyl)-5,7-

dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-

(methylsulfonyl)phenyl) propanoic acid Provided here are solid state forms of (S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-

1,2, 3, 4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl) phenyl) propanoic

acid referred herein as Compound (1), having the following structure:

Compound (1)

Samples of the solid state forms of Compound (1) were prepared according to the

processes described in examples 1 to 7 below, and were analyzed by X-ray powder

diffraction ("XRPD"). Figures 1-5 present the XRPD, of the obtained forms i, ii and iii of

Compound (1).

Figure 1: An XRPD pattern of Form i of Compound (1), prepared according to Example 1.

5 10 15 20 25 30 35

2Theta (°)

0

50

100

150

In te

ns ity

(c ps

)

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Figure 2: An XRPD pattern Form i of Compound (1), prepared according to Example 2.

Figure 3: An XRPD pattern Form i of Compound (1), prepared according to Example 3.

The crystalline form i of Compound (1) is characterized by XRPD peaks at 5.0, 5.6,

6.1, 7.3, 7.9, 8.5, 9.6, 10.0, 12.3, 12.9, 14.8, 15.9, 17.1, 17.3, 17.7, 18.1, 18.5, 18.9, 19.4,

19.7, 20.2, 20.9, 21.3, 21.7, 22.0, 22.8, 23.3, 23.6, 24.0, 24.2, 24.5, 24.7, 25.0, 25.3, 25.5,

5 10 15 20 25 30 35 2Theta (°)

0

20

40

60

80

100

120

140

In te

ns ity

(c ps

)

5 10 15 20 25 30 35 40 2Theta (°)

0

20

40

60

80

In te

ns ity

(c ps

)

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25.8, 26.2, 26.7, 27.0, 27.3, 28.2, 28.5, 29.0, 29.6, 30.4, 30.8, 31.2, 31.9, 32.3, 32.5, 33.2,

33.5, 34.0, 34.5, 35.0, 35.2, 36.0, 36.4, 36.8, 37.3, 37.8, 38.4, 38.9 and 39.5 degrees two theta

± 0.2 degrees two theta.

Figure 4: An XRPD pattern of Form ii of Compound (1)

The crystalline form ii of Compound (1) is characterized by XRPD peaks at: 5.4, 5.9,

6.3, 9.3, 10.1, 10.7, 11.0, 11.8, 12.6, 14.1, 14.7, 16.0, 16.5, 16.9, 17.8, 17.9, 18.3, 18.8, 19.2,

19.5, 20.1, 20.4, 20.8, 21.5, 22.2, 22.6, 23.1, 23.4, 23.8, 24.1, 24.4, 24.8, 25.0, 25.3, 25.8,

26.3, 26.5, 27.0, 27.6, 28.0, 28.3, 28.5, 29.1, 29.5, 29.8, 30.1, 30.6, 30.7, 31.4, 31.9, 32.3,

32.6, 33.0, 33.3, 33.6, 34.2, 34.6, 35.0, 35.3, 35.4, 36.3, 36.6, 37.0, 37.7, 38.0, 38.7, 39.2 and

39.6 degrees two theta ± 0.2 degrees two theta.

5 10 15 20 25 30 35 40 2Theta (°)

0

100

200

300

400

500

600

700

In te

ns ity

(c ps

)

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Figure 5: An XRPD pattern of Form iii of Compound (1)

The crystalline form iii of Compound (1) is characterized by XRPD peaks at: 5.0, 8.1,

9.2, 9.9, 10.7, 12.5, 12.6, 13.2, 14.3, 14.5, 14.9, 15.3, 15.4, 15.8, 16.3, 17.1, 17.4, 17.6, 18.3,

19.1, 19.3, 19.9, 20.4, 20.8, 21.1, 21.3, 21.5, 22.1, 22.7, 23.4, 24.7, 25.1, 25.3, 25.9, 26.4,

26.8, 27.3, 27.6, 28.1, 28.9, 29.2, 29.9, 30.1, 30.4, 30.8, 31.2, 31.7, 32.5, 32.8, 33.4, 33.5,

34.0, 34.4, 34.8, 35.2, 35.5, 36.2, 36.8, 37.2, 38.2, 38.6, 38.7 and 39.3 degrees two theta ± 0.2

degrees two theta.

X-ray Powder diffraction pattern ("XRPD") method:

Powder X-ray Diffraction was performed on PANalytical Empyrean X-Ray or...