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Solis state forms of (D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-, (1S)

IP.com Disclosure Number: IPCOM000241683D
Publication Date: 2015-May-21
Document File: 5 page(s) / 217K

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Solis state forms of (D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[[4-[[(3S)- tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-, (1S)

(D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3- furanyl]oxy]phenyl]methyl]phenyl]-, (1S) (referred to as Compound 1) has the following formula:

Compound 1

Figure 1: XRPD pattern of crystalline Form B of compound 1:

Main XRPD peaks of Form B:


4.7, 7.2, 11.2, 15.5, 16.6, 17.4, 19.3, 20.5, 21.4, 25.4 degrees two theta ± 0.2 degrees two theta.


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Figure 2: XRPD pattern of crystalline Form C of compound 1:

Main XRPD peaks of Form C:


3.8, 4.7, 6.8, 13.6, 15.0, 17.3, 18.2, 19.4, 20.6 and 22.7 degrees two theta ± 0.2 degrees two theta

Figure 3: XRPD pattern of crystalline Form D of compound 1:

Main XRPD peaks of Form D:


3.9, 4.9, 6.9, 9.7, 14.8, 15.2, 17.4, 19.3, 21.5 and 22.8 degrees two theta ± 0.2 degrees two theta


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X-Ray Powder Diffraction method (for Forms B and C):

X-ray powder diffraction analyses were performed on ARL X-Ray powder diffractometer model X'TRA-030; CuK_ radiation (λ = 1.5418 Å); Solid state detector with Peltier cooling, round standard aluminium sample holder with round zero background quartz plate was used. Prior to analysis, the dry samples were gently ground by means of mortar and pestle in order to obtain a fine powder. The ground sample was adjusted into a cavity of the sample holder and the surface of the sample was smoothed by means of a cover glass.

Measurement parameters:

Scan range: 2 - 40 degrees 2-theta;

Scan mode: continuous with spin;

Step size: 0.05 degrees;

Scan rate: 3 deg/min

The accuracy of peak positions is defined as +/- 0.2 degrees two-theta due to experimental differences like instrumentations, sample preparations etc…

X-Ray Powder Diffraction method (for Form D):

X-ray powder diffraction analyses were performed on Phillips X'pert PRO X-Ray powder diffractometer model; CuKα radiation (λ = 1.5418 Å); X'Celerator 2.022° 2ʘ detector , round standard aluminium sample holder with round zero background quartz plate was used. Prior to analysis, the dry samples were gently ground by means of mortar and pestle in order to obtain a fine powder. The ground sample was adjusted into a cavity of the sample holder and the surface of the sample was smoothed by means of a cover glass.

Measurement parameters:

Scan range: 2 - 40 degrees 2-theta; Scan mode: continuous with spin; Step size: 0.0167 degrees;

Time per step 37 s


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Example 1: Preparation procedure of Compound 1 Form B

1 g of Compound 1 (purity: 98.7 Area %) was dissolved at 20-25°C in 390 ml methyl ethyl ketone. The solution was filtered (0.45 µm), and cooled to -20°C and left to stand until crystallization occurred. After 4 weeks the resulted solid material was isolated by filtration. The wet isolated material was analyzed by PXRD - the PXRD pattern of the obtained form is shown in Figure 1. The remaining sample was dried on a filter at 20-25°C for 90 minutes,...