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Details for Patent: 6,335,349

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Details for Patent: 6,335,349

Title: Substituted 2(2,6-dioxopiperidin-3-yl)isoindolines
Abstract:Substituted 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)isoindolines and 1-oxo-2-(2,6-dioxo-piperidin-3-yl)isoindolines reduce the levels of TNF.alpha. in a mammal and are useful in treating oncogenic conditions, inflammation, and autoimmune diseases. Typical embodiments are 1-oxo-2-(2,6-dioxo-3-methylpiperidin-3-yl)-4,5,6,7-tetrafluoroiso-indoline and 1,3-dioxo-2-(2,6-dioxo-3-methylpiperidin-3-yl)-4-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:Nov 20, 2000
Application Number:09/716,528
Claims:1. A compound selected from the group consisting of

(a) a substantially chirally pure (R)-enantiomer, a substantially chirally pure (S)-enantiomer, or a mixture of the (R)- and (S)-enantiomers of a 2-(2,6-dioxopiperidin-3-yl)-isoindoline of the formula: ##STR7##

in which:

Y is C.dbd.O or CH.sub.2 ;

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 and R.sup.6 is alkyl of 1 to 8 carbon atoms, benzyl, or halo, or R.sup.5 is alkyl of 1 to 8 carbon atoms and R.sup.6 is hydrogen, alkyl of 1 to 8 carbon atoms, benzyl, or halo; and

(b) the acid addition salts of said 2-(2,6-dioxopiperidin-3-yl)-isoindoline.

2. A compound according to claim 1 in which R.sup.4 is --NHR.sup.5, each of R.sup.1, R.sup.2, and R.sup.3 is hydrogen, R.sup.5 is alkyl of 1 to 8 carbon atoms, and R.sup.6 is hydrogen, methyl, ethyl, or propyl.

3. A compound according to claim 2 in which Y is C.dbd.O.

4. A compound according to claim 2 in which Y is CH.sub.2.

5. A compound according to claim 1 in which R.sup.4 is amino, each of R.sup.1, R.sup.2, and R.sup.3 is hydrogen, and R.sup.6 is methyl, ethyl, or propyl.

6. A compound according to claim 5 in which Y is C.dbd.O.

7. A compound according to claim 5 in which Y is CH.sub.2.

8. A compound according to claim 7 which is 3-(1-oxo-4-aminoisoindolin-1-yl)-3-methylpiperidine-2,6-dione, 3-(1-oxo-4-aminoisoindolin-1-yl)-3-ethylpiperidine-2,6-dione, or 3-(1-oxo-4-aminoisoindolin-1-yl)-3-propylpiperidine-2,6-dione.

9. The method of reducing undesirable levels of TNF.alpha. in a mammal which comprises administering thereto an effective amount of a compound according to claim 1.

10. A method of treating an oncogenic or cancerous condition in a mammal which comprises administering thereto an effective amount of a compound according to claim 1.

11. A method of treating inflammation, inflammatory disease or autoimmune disease in a mammal which comprises administering thereto an effective amount of a compound according to claim 1.

12. A pharmaceutical composition comprising, in combination with a pharmaceutically and physiologically suitable carrier, a compound according to claim 1 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.

13. A substantially chirally pure (R)-enantiomer, a substantially chirally pure (S)-enantiomer, or a mixture of the (R)- and (S)-enantiomers of a compound of the formula: ##STR8##

in which:

Y is C.dbd.O or CH.sub.2 ;

each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is halo and R.sup.6 is alkyl of 1 to 8 carbon atoms, benzyl, or halo, or

each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms and R.sup.6 is hydrogen, alkyl of 1 to 8 carbon atoms, benzyl, or halo.

14. A compound according to claim 13 in which each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is chloro or fluoro and R.sup.6 is methyl, ethyl, or propyl.

15. A compound according to claim 14 in which Y is C.dbd.O.

16. A compound according to claim 14 in which Y is CH.sub.2.

17. A compound according to claim 13 in which each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is methyl or methoxy and R.sup.6 is hydrogen, methyl, ethyl, or propyl.

18. A compound according to claim 17 in which Y is C.dbd.O.

19. A compound according to claim 17 in which Y is CH.sub.2.

20. The method of reducing undesirable levels of TNF.alpha. in a mammal which comprises administering thereto an effective amount of a compound according to claim 13.

21. A method of treating an oncogenic or cancerous condition in a mammal which comprises administering thereto an effective amount of a compound according to claim 13.

22. A method of treating inflammation, inflammatory disease or autoimmune disease in a mammal which comprises administering thereto an effective amount of a compound according to claim 13.

23. A pharmaceutical composition comprising, in combination with a pharmaceutically and physiologically suitable carrier, a compound according to claim 13 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.
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