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US 5,605,914 AGranted
Imides
AssigneeCelgene Corporation
InventorGeorge W. Muller
Life of this patent
Estimating the term…
Abstract
Cyclic imides are inhibitors of tumor necrosis factor .alpha. and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 2-(2,6-dioxo-3-piperidinyl)-4-azaisoindoline-1,3-dione.
Claims32
A compound of the formula:
- ##STR11## in which R.sup.5 is o-phenylene, unsubstituted or substituted with 1 to 4 substituents each selected independently from nitro, cyano, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or halo;
- R.sup.7 is (i) pyridyl, (ii) phenyl substituted with one or more substituents each selected independently of the other from nitro, cyano, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, alkyl of 1 to 10 carbon atoms, alkoxy of 1 to 10 carbon atoms, or halo, (iii) benzyl unsubstituted or substituted with one to three substituents selected from the group consisting of nitro, cyano, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or halo, (iv) naphthyl, (v) benzyloxy, or (vi) imidazol-4-ylmethyl;
- each of R.sup.8' and R.sup.9', independently of the other, is hydrogen or alkyl of 1 to 10 carbon atoms;
- and
- n has a value of 0, 1, 2, or 3.
2 more elements
A compound of the formula:
- ##STR12## in which R.sup.5 is o-phenylene, unsubstituted or substituted with 1 to 4 substituents each selected independently from nitro, cyano, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or halo;
- R.sup.7 is (i) pyridyl, (ii) phenyl substituted with one or more substituents each selected independently of the other from nitro, cyano, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, alkyl of 1 to 10 carbon atoms, alkoxy of 1 to 10 carbon atoms, or halo, (iii) benzyl unsubstituted or substituted with one to three substituents selected from the group consisting of nitro, cyano, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or halo, (iv) naphthyl, (v) benzyloxy, or (vi) imidazol-4-ylmethyl;
- R.sup.12 is hydroxy or alkoxy of 1 to 12 carbon atoms;
- and
- n has a value of 0, 1, 2, or 3.
2 more elements
A compound of the formula:
- ##STR13## in which R.sup.5 is o-phenylene, unsubstituted or substituted with 1 to 4 substituents each selected independently from nitro, cyano, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or halo;
- R.sup.7 is (i) pyridyl, (ii) phenyl substituted with one or more substituents each selected independently of the other from nitro, cyano, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, alkyl of 1 to 10 carbon atoms, alkoxy of 1 to 10 carbon atoms, or halo, (iii) benzyl unsubstituted or substituted with one to three substituents selected from the group consisting of nitro, cyano, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or halo, (iv) naphthyl, (v) benzyloxy, or (vi) imidazol-4-ylmethyl;
- R.sup.12 is --OH, alkoxy of 1 to 12 carbon atoms, --O--CH.sub.2 -pyridyl, --O--benzyl, or ##STR14## in which:
- R.sup.8' is hydrogen or alkyl of 1 to 10 carbon atoms;
- and
- R.sup.9' is hydrogen, alkyl of 1 to 10 carbon atoms, --CH.sub.2 -pyridyl, benzyl, --COR10, or --SO.sub.2 R10 in which R10 is hydrogen, alkyl of 1 to 4 carbon atoms, or phenyl;
- and
- n has a value of 0, 1, 2, or 3.
5 more elements
Dependencies are inferred from the claim text.