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Solid state forms of 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, (2E)-2-[1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]-2-hydroxyethylidene]hydrazide

IP.com Disclosure Number: IPCOM000250551D
Publication Date: 2017-Aug-02
Document File: 5 page(s) / 316K

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The IP.com Prior Art Database

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Solid state forms of 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, (2E)-2-[1-

[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-

2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]-2-

hydroxyethylidene]hydrazide

Provided here are solid state forms of 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-,

(2E)-2-[1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-

hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]-2-

hydroxyethylidene]hydrazide 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 3 below, and were analyzed by X-ray powder diffraction

("XRPD") method. Figures 1 to 3 present the XRPD patterns of the obtained forms A and B of

Compound (1).

Compound (1) may be hydrochloric acid salt.

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

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

5 10 15 20 25 30 35 40 2Theta (°)

0

20

40

60

80

100

120

140

In te

n s it y (

c p

s )

5 10 15 20 25 30 35 40 2Theta (°)

0

10

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30

40

In te

n s it y (

c p

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

The crystalline form A of Compound (1) as depicted in Figure 1 is characterized by XRPD

peaks at 6.6, 9.3, 13.3, 14.9, 16.3, 17.4, 18.0, 19.2, 20.3, 20.9, 23.0, 24.3, 25.0, 27.2, 29.4,

31.3, 32.3, 34.8 and 37.5 degrees two theta ± 0.2 degrees two theta.

Eventually, form A of Compound (1) of low degree of crystallinity as depicted in Figure 2 is

characterized by broad XRPD peaks at 6.6, 13.5, 15.3 and 18.2 ± 0.4 degrees two theta.

The crystalline form B of Compound (1) as depicted in Figure 3 is characterized by XRPD

peaks at 5.9, 6.7, 9.0, 10.4, 11.7, 14.2, 15.3, 17.6, 17.7, 18.6, 19.4, 20.1, 20.8, 21.5, 22.3, 23.5,

24.5, 25.3, 25.6, 26.7, 27.3, 28.1, 29.4, 30.3, 31.5, 33.1, 33.5, 34.6, 35.5, 36.3, 37.6, 38.3 and

39.2 degrees two theta ± 0.2 degrees two theta.

5 10 15 20 25 30 35 40 2Theta (°)

0

200

400

600I n

te n

s it y (

c p

s )

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

Powder X-ray diffraction was measured on PANalytical X’Pert Pro powder diffractometer

equipped with X'Celerator detector at CuKα radiation (λ = 1.541874 Å) and at laboratory

temperature 25 ± 2 °C. Prior to analysi...