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US 5,665,754 AGranted
Substituted pyrrolidines
AssigneeGlaxo Wellcome Inc.
InventorsPaul Lawrence Feldman, Jeffrey Alan Stafford
Life of this patent
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Abstract
Novel pyrrolidine compounds which are useful for inhibiting the function of Type IV phosphodiesterase (PDE-IV) as well as methods for making the same are disclosed. Applications in treating inflammatory diseases and other diseases involving elevated levels of cytokines, as well as central nervous system (CNS) disorders, are also disclosed.
Claims26
A compound of Formula (I) ##STR10## wherein:
- R.sup.1 is alkyl, haloalkyl, cycloalkyl, bridged polycycloalkyl, aryl, aralkyl, heteroaralkyl, aryloxyalkyl or a 5 to 6-membered heterocyclic aromatic group optionally fused to a benzene ring and optionally substituted with one or more substituents selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
- R.sup.2 is H, alkyl, haloalkyl, cycloalkyl, aryl, --CO-alkyl, --CO-cycloalkyl, --CO-aryl, --COO-alkyl, --COO-cycloalkyl, --COO-aryl, CH.sub.2 OH, CH.sub.2 --O-alkyl, --CHO, --CN, --NO.sub.2 or SO.sub.2 R.sup.10 ;
- R.sup.3 is --CO-alkyl, --CO-haloalkyl, --CO-cycloalkyl, --COO-alkyl, --COO-cycloalkyl, --COOH, --CO-aryl, --CONR.sup.6 R.sup.7, --CH.sub.2 OH, --CH.sub.2 O-alkyl, --CHO, --CN, --NO.sub.2, --NR.sup.8 COR.sup.9, --NR.sup.8 SO.sub.2 R.sup.10 or --SO.sub.2 R.sup.10 ;
- R.sup.4 is H, alkyl, haloalkyl, cycloalkyl, --CO-alkyl, --CO-haloalkyl, --CO-cycloalkyl, --COO-alkyl, --COO-cycloalkyl, --COOH, --CO-aryl, --CONR.sup.6 R.sup.7, --CN, --CHO or SO.sub.2 R.sup.10 ;
- R.sup.5 is --CN or --C(X)--R.sup.11 or SO.sub.2 R.sup.10 ;
- R.sup.6 and R.sup.7 are independently selected from H, alkyl, cycloalkyl, aryl or aralkyl or R.sup.6 and R.sup.7 together form a 4- to 7-membered heterocyclic or carbocyclic ring;
- R.sup.8 is H, alkyl or cycloalkyl;
- R.sup.9 is alkyl, cycloalkyl, aryl, alkoxy, aralkoxy or --NR.sup.6 R.sup.7 ;
- R.sup.10 is alkyl, cycloalkyl, trifluoromethyl, aryl, aralkyl or --NR.sup.6 R.sup.7 ;
- R.sup.11 is H, alkyl, haloalkyl, cycloalkyl, aryl, aralkyl, C.sub.1-6 alkoxy, aralkoxy, aryloxy, --NR.sup.6 R.sup.7 or a 5 to 6-membered heterocyclic aromatic group optionally fused to a benzene ring and optionally substituted with one or more substituents selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
- R.sup.12 is C.sub.1-3 alkyl, cyclopropyl or C.sub.1-3 haloalkyl;
- and
- X is O or S.
10 more elements
Dependencies are inferred from the claim text.