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Last Updated: March 28, 2024

Details for Patent: 6,476,052


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Title: Isoindolines, method of use, and pharmaceutical compositions
Abstract:Substituted 1-oxo-2-(2,6-dioxopiperidin-3-yl)isoindolines are useful in treating inflammation, inflammatory disease, autoimmune disease, and oncogenic or cancerous conditions in a mammal. Typical embodiments are 1-oxo-2-(2,6-dioxopiperidin-3yl)4-aminoisoindoline and 1-oxo-2-(2,6-dioxo-3-methylpiperidin-3-yl)aminoisoindoline.
Inventor(s): Muller; George W. (Bridgewater, NJ), Stirling; David I. (Branchburg, NJ), Chen; Roger Shen-Chu (Edison, NJ)
Assignee: Celgene Corporation (Warren, NJ)
Filing Date:Aug 07, 2000
Application Number:09/633,908
Claims:1. A method of treating inflammation, inflammatory disease or autoimmune disease in a mammal which comprises administering thereto an effective amount of a compound of the formula: ##STR7##

in which: each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4, independently of the others, is halo, alkyl of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms or (ii) one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is --NHR.sup.5 and the remaining of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are hydrogen; R.sup.5 is hydrogen or alkyl of 1 to 8 carbon atoms; R.sup.6 is hydrogen, alkyl of 1 to 8 carbon atoms, benzyl, or halo; or

an acid addition salt of said compound which contain a nitrogen atom capable of being protonated.

2. The method according to claim 1 wherein said disease is rheumatoid arthritis.

3. The method according to claim 1 wherein said disease is osteoarthritis.

4. The method according to claim 1 wherein said disease is inflammatory bowel disease.

5. The method according to claim 4 wherein said inflammatory bowel disease is Crohn's disease.

6. The method according to claim 4 wherein said inflammatory bowel disease is ulcerative colitis.

7. The method according to claim 1 wherein said disease is an arthritic condition.

8. The method according to claim 1 wherein said disease is sepsis.

9. The method according to claim 1 wherein said disease is lupus.

10. The method according to claim 1 wherein said disease is erythema nodosum leprosum.

11. The method of claim 1 wherein said compound is administered orally.

12. The method of claim 1 wherein said compound is administered parenterally.

13. The method according to claim 1 in which said compound is administered in combination with a therapeutic agent.

14. The method of claim 13 wherein said therapeutic agent is a steroid, antibiotic or neoplastic agent.

15. A method of treating an oncogenic or cancerous condition in a mammal ##STR8##

which comprises administering thereto an effective amount of a compound of the formula:

in which: each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4, independently of the others, is halo, alkyl of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms or (ii) one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is --NHR.sup.5 and the remaining of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are hydrogen; R.sup.5 is hydrogen or alkyl of 1 to 8 carbon atoms; R.sup.6 is hydrogen, alkyl of 1 to 8 carbon atoms, benzyl, or halo; or

an acid addition salt of said compound which contain a nitrogen atom capable of being protonated.

16. The method of claim 15 wherein said compound is administered orally.

17. The method according to claim 15 wherein said compound is administered parenterally.

18. The method of claim 15 in which said compound is administered in combination with a therapeutic agent.

19. The method of claim 18 wherein said therapeutic agent is a steroid, neoplastic agent or antibiotic.

20. A method of reducing undesirable levels of TNF.alpha. in a mammal which comprises administering thereto an effective amount of a compound of the formula: ##STR9##

in which: each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4, independently of the others, is halo, alkyl of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms or (ii) one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is --NHR.sup.5 and the remaining of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are hydrogen; R.sup.5 is hydrogen or alkyl of 1 to 8 carbon atoms; R.sup.6 is hydrogen, alkyl of 1 to 8 carbon atoms, benzyl, or halo; or

an acid addition salt of said compound which contain a nitrogen atom capable of being protonated.

21. The method of claim 20 wherein said compound is administered orally.

22. The method of claim 20 wherein said compound is administered parenterally.

23. The method of claim 20 in which said compound is administered in combination with a therapeutic agent.

24. The method of claim 23 wherein said therapeutic agent is a steroid, neoplastic agent or antibiotic.

25. A pharmaceutical composition comprising, in combination with a pharmaceutically and physiologically suitable carrier, a compound of the formula: ##STR10##

in which: each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4, independently of the others, is halo, alkyl of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms or (ii) one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is --NHR.sup.5 and the remaining of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are hydrogen; R.sup.5 is hydrogen or alkyl of 1 to 8 carbon atoms; R.sup.6 is hydrogen, alkyl of 1 to 8 carbon atoms, benzyl, or halo; or

an acid addition salt of said compound which contain a nitrogen atom capable of being protonated, in a quantity sufficient upon administration in a single or multiple dose regimen to a mammal to produce at least one of the effects of reducing the level of TNF.alpha., improving an oncogenic or cancerous condition, reducing inflammation, or improving autoimmune disease.

26. The pharmaceutical composition according to claim 25 in which said dosage form is selected from the group consisting of powder, tablets, capsules and injectable compositions.

27. The pharmaceutical composition of claim 26 which is administered in combination with a therapeutic agent.

28. The pharmaceutical composition of claim 26 wherein said therapeutic agent is a steroid, antibiotic or neoplastic agent.

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