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US 7,256,198 B2Granted
Pyrimidoindolones and methods for using same
AssigneeWyeth
InventorsPaul Jeffrey Dollings, Arlene Joan Dietrich, Lisa Marie Havran, Chae-Koo Dan Chong, Donna Mary Huryn, Albert Jean Robichaud, Boyd Lynn Harrison, Wayne Everett Childers, Alexander A. Greenfield, James Jacob Bicksler, Vasilios Marathias
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Abstract
Novel pyrimidoindolone compounds are disclosed. Methods of using the pyrimidoindolone compounds and compositions containing the compounds in the treatment and/or prevention of disease and other conditions related to inflammation, neurodegeneration, osteoarthritis and apoptosis are also disclosed.
Claims29
A compound of formula I:
- or a stereoisomer, or pharmaceutically-acceptable salt thereof;
- wherein:
- R1 and R2 are independently hydrogen, halogen, alkyl, aryl, heteroaryl, or R1 and R2 together with the carbon atom to which they are attached, form a C3-C7 carbocyclyl or a C3-C7 heterocycle;
- R3 and R17 are independently, hydrogen and alkyl;
- R15 and R16 are independently, hydrogen, alkyl, or aryl, provided that R15 and R16 are not both aryl;
- R4 is hydrogen, halogen, alkyl, nitrile, carboxyl, hydroxy, amino, R7R8N—, alkoxy, or perfluoroalkoxy;
- X is cyano, perfluoroalkoxy,
- R5is alkyl, aryl, heteroaryl, heterocycle, or carbocyclyl;
- R6 is hydrogen or C1-C3 alkyl;
- R7 and R8 are independently hydrogen, alkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, alkanoyl, perfluoroalkanoyl, aroyl, heteroaroyl, aralkanoyl, heteroaralkanoyl, or R7 and R8 together with the nitrogen to which they are attached form a 5 to 10 member optionally substituted monocyclic or bicyclic ring system, which may further contain heteroatoms selected from oxygen, nitrogen or sulfur, provided that no ring may contain more than 3 heteroatoms;
- and
- R9 is hydrogen, alkyl, aryl, heteroaryl, aralkyl, C4-C12 heteroaralkyl, or C3-C12 carbocyclyl.
9 more elements
A method comprising contacting a caspase with a compound of formula I:
- or a, stereoisomer, or pharmaceutically-acceptable salt thereof;
- wherein:
- R1 and R2 are independently hydrogen, halogen, alkyl, aryl, heteroaryl, or R1 and R2 together with the carbon atom to which they are attached, form a C3-C7 carbocyclyl or a C3-C7 heterocycle;
- R3 and R17 are independently, hydrogen and alkyl;
- R15 and R16 are independently hydrogen, alkyl, or aryl, provided that R15 and R16 are not both aryl;
- R4 is hydrogen, halogen, alkyl, nitro, nitrile, carboxyl, hydroxy, amino, R7R8N—, alkoxy, or perfluoroalkoxy;
- X is nitro, cyano, alkyl, perfluoroalkoxy, halogen,
- R5 is alkyl, aryl, heteroaryl, heterocycle, or carbocyclyl;
- R6 is hydrogen or C1-C3 alkyl;
- R7 and R8 are independently hydrogen, alkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, alkanoyl, perfluoroalkanoyl, aroyl, heteroaroyl, aralkanoyl, heteroaralkanoyl, or R7 and R8 together with the nitrogen to which they are attached form a 5 to 10 member optionally substituted monocyclic or bicyclic ring system, which may further contain heteroatoms selected from oxygen, nitrogen or sulfur, provided that no ring may contain more than 3 heteroatoms;
- and
- R9 is hydrogen, alkyl, aryl, heteroaryl, aralkyl, C4-C12 heteroaralkyl, or C3-C12 carbocyclyl.
9 more elements
A compound of formula II:
- or a prodrug, stereoisomer, or pharmaceutically-acceptable salt thereof;
- wherein:
- R1 and R2 are independently hydrogen, halogen, alkyl, aryl, heteroaryl, or R1 and R2 together with the carbon atom to which they are attached, form a C3-C7 carbocyclyl or a C3-C7 heterocycle;
- R3 and R17 are independently hydrogen or alkyl;
- R15 and R16 are independently, hydrogen, alkyl, or aryl, provided that R15 and R16 are not both aryl;
- R4 is hydrogen, halogen, alkyl, nitro, nitrile, carboxyl, hydroxy, amino, R7R8N—, alkoxy, or perfluoroalkoxy;
- X is nitro, cyano, alkyl, perfluoroalkoxy, halogen,
- R5 is alkyl, aryl, heteroaryl, heterocycle, or carbocyclyl;
- R6 is hydrogen or C1-C3 alkyl;
- R7 and R8 are independently hydrogen, alkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, alkanoyl, perfluoroalkanoyl, aroyl, heteroaroyl, aralkanoyl, heteroaralkanoyl, or R7 and R8 together with the nitrogen to which they are attached form a 5 to 10 member optionally substituted monocyclic or bicyclic ring system, which may further contain heteroatoms selected from oxygen, nitrogen or sulfur, provided that no ring may contain more than 3 heteroatoms;
- R9 is hydrogen, alkyl, aryl, heteroaryl, aralkyl, C4-C12 heteroaralkyl, or C3-C12 carbocyclyl;
- and
- n is an integer of 0 or 1.
10 more elements
Dependencies are inferred from the claim text.