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Crystalline forms of Vilazodone & Vilazodone HCl

IP.com Disclosure Number: IPCOM000240099D
Publication Date: 2014-Dec-31

Publishing Venue

The IP.com Prior Art Database

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Vilazodone Hydrochloride, 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzofurancarboxamide hydrochloride, having the structure shown in Formula-I, has been  approved under the trade name VIBRYD® by the United States Food and Drug Administration. VIBRYD® is indicated for the treatment of major depressive disorder.

 

Example 1: Preparation of Vilazodone crystalline form B

Vilazodone (3 g) was suspended in a 1:1 mixture of methanol and toluene (160 ml) at 25-30°C. The suspension was heated to 60-65°C, maintained for 0.5 hour and the resulting hazy solution was filtered to remove undissolved particulate. The clear solution was further heated to 60-65°C and maintained for 1 hour at 60-65°C and cooled to 25-30°C. The resulting solid was filtered and dried under vacuum at 40°C for 4 hours to yield Vilazodone Form B.

                           

                    Powder X-ray diffraction pattern of crystalline Vilazodone Form-B               

                                                                            

       

    DSC thermogram of Vilazodone Form-B

                                                                                                                                                                   

TGA of Vilazodone Form-B                         

Example 2: Process for the preparation of Vilazodone crystalline Form-C

Vilazodone base (10g) was suspended in acetic acid (40 ml) at 25-30°C. The suspension was stirred for 10 mints to get clear solution. Filter the clear solution trough hyflow and bed wash with 10 ml acetic acid. To the clear solution, slowly add water (200ml) at 25-30oC and maintained under agitation for 2h.  The resulting solid was filtered washed with water (20ml) and dried under vacuum at 40°C for 5h to yield Vilazodone crystalline Form-C.

Example 3: Process for the preparation of Vilazodone crystalline Form-C

Vilazodone base (10g) was suspended in acetic acid (40 ml) at 25-30°C and heated to 40-45oC. The suspension was stirred for 10 minutes to get clear solution. Filter the clear solution trough hyflo and bed wash with 10 ml acetic acid. To the clear solution, slowly add water (200ml) at 40-45oC and maintained under agitation for 2h. The resulting solid filtered washed with water (20ml) and dried under vacuum at 40°C for 5h to yield Vilazodone crystalline Form-C.

Powder X-ray diffraction pattern of crystalline Vilazodone Form-C

DSC thermogram of Vilazodone Form-C

                   

TGA of Vilazodone Form-C

Example 4: Process for the preparation of Vilazodone crystalline Form-D

Vilazodone Form-C was dried under vacuum at 40oC for 96...