IP Library Granted Patent US 9,884,042
Granted Patent B2
US 9,884,042 · App. 14/344,870 · Granted Feb 6, 2018

Formulations of cyclopropanecarboxylic acid {2-[(1S)-1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide

Inventors: Nathan Boersen (Morristown, NJ); Wai Yip Lee (Bedminster, NJ); Ho-Wah Hui (Basking Ridge, NJ); Paul Kurtulik (Branchburg, NJ)
Assignee: Celgene Corporation
A61K31/4035A61K9/10A61K9/146
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,884,042
App. No.
14/344,870
Granted
Feb 6, 2018
Kind
B2
Abstract

Pharmaceutical compositions and single unit dosage forms of {2-[(IS)-1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide, or a pharmaceutically acceptable stereoisomer, prodrug, salt, solvate, hydrate, or clathrate thereof, are provided herein. Also provided are methods of treating, managing, or preventing various disorders, such as cancer or an inflammatory disease.

Claims (17)

1. An oral dosage form comprising: 1) an amorphous solid dispersion of a compound of formula (I):

or a pharmaceutically acceptable salt thereof, in a hydrophilic polymer; and 2) a pharmaceutically acceptable carrier or excipient; and

wherein the dosage form comprises from about 5% to about 10% by weight of the compound of formula (I);

wherein the dispersion consists of from about 15% to about 25% by weight of the compound of formula (I) and from about 75% to about 85% by weight of hydrophilic polymer;

wherein the dosage form comprises from about 33% to about 67% percent by weight of the amorphous solid dispersion; and

wherein the dosage form comprises 24% by weight of microcrystalline cellulose; wherein maximum-compactibility grade microcrystalline cellulose is present at an amount of 10% by weight of the total dosage form and the remaining portion of the microcrystalline cellulose is of a lower compactibility grade than the maximum-compactibility grade.

2. The oral dosage form of claim 1 , wherein the amorphous solid dispersion is prepared by hot melt extrusion, lyophilization, spray drying, solvent casting, or melt quenching.

3. The oral dosage form of claim 1 , wherein the hydrophilic polymer is hydroxypropyl methylcellulose, polyvinylpyrrolidone, hydroxypropyl cellulose, PVP VA64, hydroxypropyl methylcellulose acetate succinate, Eudragit polymers, polyvinylacetate, Polyox, Soluplus, or polyethylene glycol.

4. The oral dosage form of claim 1 , wherein the hydrophilic polymer is hydroxypropyl methylcellulose.

5. The oral dosage form of claim 1 , wherein the carrier or excipient is selected from the group consisting of, mannitol, sodium croscarmellose, calcium stearate, crospovidone, polyvinyl alcohol, magnesium stearate, anhydrous lactose, silicon dioxide, fructose, hydroxypropyl methylcellulose, polyvinylpyrrolidone, hydroxypropyl cellulose, and combinations thereof.

6. The oral dosage form of claim 1 , wherein the dosage form comprises about 5% by weight of the compound of formula (I).

7. The oral dosage form of claim 1 , wherein the amorphous solid dispersion consists of about 15% by weight of the compound of formula (I) and about 85% by weight of hydrophilic polymer.

8. The oral dosage form of claim 1 , wherein the dosage form comprises about 33% by weight of the dispersion.

9. The oral dosage form of claim 1 , wherein the dosage form consists of about 5% by weight of the compound of formula (I) and about 28% by weight of hydroxypropyl methyl cellulose, which together comprise the dispersion; 24% by weight of microcrystalline cellulose; about 36% by weight of mannitol; about 5% by weight of sodium croscarmellose; and about 1% by weight of calcium stearate or magnesium stearate; wherein the microcrystalline cellulose is maximum-compactibility grade microcrystalline cellulose present at an amount of 10% by weight of the total dosage form and the remaining portion of the microcrystalline cellulose is of a lower compactibility grade than the maximum-compactibility grade.

10. The oral dosage form of claim 9 , wherein the amorphous solid dispersion is prepared by hot melt extrusion.

11. The oral dosage form of claim 1 , wherein the lower compactibility grade microcrystalline cellulose is Avicel PH-102.

12. The oral dosage form of claim 9 , wherein the lower compactibility grade microcrystalline cellulose is Avicel PH-102.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 4, 2019
From: CELGENE CORPORATION
To: AMGEN INC.
Reel/Frame 051181/0038 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2015
From: BOERSEN, NATHAN; LEE, WAI YIP; HUI, HO-WAH; KURTULIK, PAUL
To: CELGENE CORPORATION
Reel/Frame 035473/0318 →
Continuity (2)
Provisional Application 61534841 · Sep 14, 2011
Related Publication 20150190374A1 · Jul 9, 2015