IP Library Granted Patent US 9,283,207
Granted Patent B2
US 9,283,207 · App. 14/316,160 · Granted Mar 15, 2016

Methods of using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione

Inventors: George W. Muller (Rancho Santa Fe, CA); Peter H. Schafer (Belle Mead, NJ); Hon-Wah Man (Princeton, NJ); Chuansheng Ge (Belle Mead, NJ)
Assignee: Celgene Corporation
A61K31/4035A61K45/06C07C317/28C07D209/48C07B2200/07
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Quick Facts
Patent No.
US 9,283,207
App. No.
14/316,160
Granted
Mar 15, 2016
Kind
B2
Abstract

Stereomerically pure (+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, substantially free of its (−) isomer, and prodrugs, metabolites, polymorphs, salts, solvates, hydrates, and clathrates thereof are discussed. Also discussed are methods of using and pharmaceutical compositions comprising the (+) enantiomer of 2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione are disclosed. The methods include methods of treating and/or preventing disorders ameliorated by the reduction of levels of TNF-α or the inhibition of PDE4.

Claims (24)

1. A method of treating a disease or disorder selected from Crohn's Disease or ulcerative colitis, the method comprising administering to a patient having a Crohn's Disease or ulcerative colitis a therapeutically effective amount of a compound which is stereomerically pure (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, or a pharmaceutically acceptable salt thereof.

2. The method of claim 1 further comprising administering to the patient a therapeutically effective amount of an antihistamine, anti-inflammatory drug, non-steroid anti-inflammatory drug, or steroid.

3. The method of claim 1 wherein the compound is administered parenterally, transdermally, mucosally, nasally, buccally, sublingually, or orally.

4. The method of claim 3 wherein the compound is administered orally.

5. The method of claim 4 wherein the compound is administered orally in a tablet or capsule form.

6. The method of claim 1 wherein the therapeutically effective amount is from about 1 mg to about 1000 mg per day.

7. The method of claim 6 wherein the therapeutically effective amount is from about 5 mg to about 500 mg per day.

8. The method of claim 7 wherein the therapeutically effective amount is from about 10 mg to about 200 mg per day.

9. The method of claim 1 , wherein the disease or disorder is Crohn's Disease.

10. The method of claim 1 , wherein the disease or disorder is ulcerative colitis.

11. The method of claim 4 , wherein the compound is administered twice daily in equally divided doses.

12. The method of claim 4 , wherein the stereomerically pure compound comprises greater than about 90% by weight of (+) isomer based on the total weight percent of the compound.

13. The method of claim 4 , wherein the stereomerically pure compound comprises greater than about 95% by weight of (+) isomer based on the total weight percent of the compound.

14. The method of claim 4 , wherein the stereomerically pure compound comprises greater than about 97% by weight of (+) isomer based on the total weight percent of the compound.

15. The method of claim 5 , wherein the capsule contains about 10 mg of the compound.

16. The method of claim 5 , wherein the capsule contains about 20 mg of the compound.

17. The method of claim 5 , wherein the capsule contains about 25 mg of the compound.

18. The method of claim 5 , wherein the capsule contains about 50 mg of the compound.

19. The method of claim 5 , wherein the tablet contains about 10 mg of the compound.

20. The method of claim 5 , wherein the tablet contains about 20 mg of the compound.

21. The method of claim 5 , wherein the tablet contains about 25 mg of the compound.

22. The method of claim 5 , wherein the tablet contains about 50 mg of the compound.

23. A method of treating Crohn's Disease, which comprises orally administering to a patient having Crohn's Disease about 10 mg to about 100 mg of a compound which is stereomerically pure (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione comprising greater than about 97% by weight of (+) isomer, wherein the compound is administered in the form of a tablet or capsule twice daily in equally divided doses.

24. A method of treating ulcerative colitis, which comprises orally administering to a patient having ulcerative colitis about 10 mg to about 100 mg of a compound which is stereomerically pure (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione comprising greater than about 97% by weight of (+) isomer, wherein the compound is administered in the form of a tablet or capsule twice daily in equally divided doses.

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 Jun 26, 2014
From: MULLER, GEORGE W.; SCHAFER, PETER H.; MAN, HON-WAH; GE, CHUANSHENG
To: CELGENE CORPORATION
Reel/Frame 033245/0592 →
Continuity (8)
Continuation 13682652 · Nov 20, 2012
Continuation 12630788 · Dec 3, 2009
Continuation 12098379 · Apr 4, 2008
Division 11170308 · Jun 28, 2005
Division 10392195 · Mar 19, 2003
Provisional Application 60438450 · Jan 7, 2003
Provisional Application 60366515 · Mar 20, 2002
Related Publication 20140371287A1 · Dec 18, 2014