Solid forms of 2-(4-chlorophenyl)-N-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)-2,2-difluoroacetamide, and their pharmaceutical compositions and uses

Patent metadata

Field	Value
Publication number	US-10189808-B2
Application number	US-201715400630-A
Country	US
Kind code	B2
Filing date	Jan 6, 2017
Priority date	Jan 8, 2016
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

Solid forms comprising 2-(4-chlorophenyl)-N-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)-2,2-difluoroacetamide, compositions comprising the solid forms, methods of making the solid forms and methods of their uses are disclosed.

First claim

What is claimed is:

1. A solid form of 2-(4-chlorophenyl)-N-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)-2,2-difluoroacetamide or a tautomer thereof, which is Form C having an X-ray powder diffraction pattern comprising peaks at about 16.7, 16.9, 17.7 or 24.7 degrees 2θ.

2. The solid form of claim 1 , having an X-ray powder diffraction pattern comprising peaks at about 7.4, 11.5, 15.8, 16.7, 16.9, 17.7, 18.4, 19.2, 19.5, 21.1, 23.4, 24.7, or 29.9 degrees 2θ.

3. The solid form of claim 1 , having an X-ray powder diffraction pattern substantially as shown in FIG. 16 .

4. The solid form of claim 1 , having a thermal gravimetric analysis plot substantially as shown in FIG. 18 .

5. The solid form of claim 1 , having a differential scanning calorimetry plot comprising a melting event with an onset temperature of about 232° C.

6. The solid form of claim 1 , having a differential scanning calorimetry plot substantially as shown in FIG. 19 .

7. The solid form of claim 1 , which exhibits a mass increase of less than about 0.6% when subjected to an increase in relative humidity from about 0% to about 90% relative humidity.

8. The solid form of claim 1 which is substantially pure.

9. The solid form of claim 1 , which is anhydrous.

10. A pharmaceutical composition comprising the solid form of claim 1 and a pharmaceutically acceptable carrier, diluent or excipient.

Assignees

• Celgene Corp

Inventors

• Fernandez Paul F
• Ferretti Antonio C
• Kothare Mohit A
• Li Ying
• Man Hon-Wah
• Zhang Weihong

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P35/02

  specific for leukemia · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61K9/19

  lyophilised {, i.e. freeze-dried, solutions or dispersions (lyophilised products with subsequent particle size reduction A61K9/14; granules or pellets made by lyphilisation A61K9/1682; solid oral dosage forms made by lyophilisation A61K9/2095; lyophilisation additives A61K47/00)} · CPC title

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title