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US 5,514,706 AGranted
Pharmaceutical compounds
AssigneeEli Lilly and Company
InventorsSamantha J. Ambler, William F. Heath, Jr., Jai P. Singh, Colin W. Smith, Lawrence E. Stramm
Life of this patent
Estimating the term…
Abstract
This invention provides novel compounds and pharmaceutical methods comprising the administration of a compound of the Formula I: ##STR1## wherein n, m, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are variables.
Claims4
A method of treating diabetic complications, which comprises administering to a patient in need of treatment an effective amount of a compound of the Formula I:
- ##STR11## wherein n and m are independently 0, 1 or 2;
- R.sub.1 is halo, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, hydroxy-C.sub.1 -C.sub.4 alkyl, hydroxy-C.sub.1 -C.sub.4 alkoxy, trifluoromethoxy, carboxy, --COOR.sub.5 where R.sub.5 is a C.sub.1 -C.sub.4 alkyl, --COR.sub.6, --CONR.sub.6 R.sub.7 or --NR.sub.6 R.sub.7 where R.sub.6 and R.sub.7 are each hydrogen or C.sub.1 -C.sub.4 alkyl;
- R.sub.2 is halo, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, hydroxy-C.sub.1 -C.sub.4 alkyl, hydroxy-C.sub.1 -C.sub.4 alkoxy, trifluoromethoxy, carboxy, --COOR.sub.8 where R.sub.8 is a C.sub.1 -C.sub.4 alkyl, --COR.sub.9, --CONR.sub.9 R.sub.10 or --NR.sub.9 R.sub.10 where R.sub.9 and R.sub.10 are each hydrogen or C.sub.1 -C.sub.4 alkyl;
- R.sub.3 is nitrile, carboxy or --COOR.sub.11 where R.sub.11 is a C.sub.1 -C.sub.4 alkyl;
- and
- R.sub.4 is --NR.sub.12 R.sub.13, --NR.sub.12 COR.sub.13, --N(COR.sub.12).sub.2, --N.dbd.CHOCH.sub.2 R.sub.12, ##STR12## or 1-pyrrolyl;
- wherein R.sub.12 and R.sub.13 are each hydrogen or C.sub.1 -C.sub.4 alkyl;
- X is C.sub.2 -C.sub.4 alkylene;
- wherein 1-pyrrolyl is optionally substituted with one or two moieties selected from the group consisting of C.sub.1 -C.sub.4 alkyl, carboxy, hydroxy-C.sub.1 -C.sub.4 alkyl, or --CHO;
- or a pharmaceutically-acceptable salt thereof.
7 more elements
A method of inhibiting endothelial cell activation, which comprises administering to a patient in need of treatment an effective amount of a compound of the Formula I:
- ##STR13## wherein n and m are independently 0, 1 or 2;
- R.sub.1 is halo, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, hydroxy-C.sub.1 -C.sub.4 alkyl, hydroxy-C.sub.1 -C.sub.4 alkoxy, trifluoromethoxy, carboxy, --COOR.sub.5 where R.sub.5 is a C.sub.1 -C.sub.4 alkyl, --COR.sub.6, --CONR.sub.6 R.sub.7 or --NR.sub.6 R.sub.7 where R.sub.6 and R.sub.7 are each hydrogen or C.sub.1 -C.sub.4 alkyl;
- R.sub.2 is halo, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, hydroxy-C.sub.1 -C.sub.4 alkyl, hydroxy-C.sub.1 -C.sub.4 alkoxy, trifluoromethoxy, carboxy, --COOR.sub.8 where R.sub.8 is a C.sub.1 -C.sub.4 alkyl, --COR.sub.9, --CONR.sub.9 R.sub.10 or --NR.sub.9 R.sub.10 where R.sub.9 and R.sub.10 are each hydrogen or C.sub.1 -C.sub.4 alkyl;
- R.sub.3 is nitrile, carboxy or --COOR.sub.11 where R.sub.11 is a C.sub.1 -C.sub.4 alkyl;
- and
- R.sub.4 is --NR.sub.12 R.sub.13, --NR.sub.12 COR.sub.13, --N(COR.sub.12).sub.2, --N.dbd.CHOCH.sub.2 R.sub.12, ##STR14## or 1-pyrrolyl;
- wherein R.sub.12 and R.sub.13 are each hydrogen or C.sub.1 -C.sub.4 alkyl;
- X is C.sub.2 -C.sub.4 alkylene;
- wherein 1-pyrrolyl is optionally substituted with one or two moieties selected from the group consisting of C.sub.1 -C.sub.4 alkyl, carboxy, hydroxy-C.sub.1 -C.sub.4 alkyl, or --CHO;
- or a pharmaceutically-acceptable salt thereof.
7 more elements
A method of treating vascular dysfunction, which comprises administering to a patient in need of treatment an effective amount of a compound of the Formula I:
- ##STR15## wherein n and m are independently 0, 1 or 2;
- R.sub.1 is halo, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, hydroxy-C.sub.1 -C.sub.4 alkyl, hydroxy-C.sub.1 -C.sub.4 alkoxy, trifluoromethoxy, carboxy, --COOR.sub.5 where R.sub.5 is a C.sub.1 -C.sub.4 alkyl, --COR.sub.6, --CONR.sub.6 R.sub.7 or --NR.sub.6 R.sub.7 where R.sub.6 and R.sub.7 are each hydrogen or C.sub.1 -C.sub.4 alkyl;
- R.sub.2 is halo, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, hydroxy-C.sub.1 -C.sub.4 alkyl, hydroxy-C.sub.1 -C.sub.4 alkoxy, trifluoromethoxy, carboxy, --COOR.sub.8 where R.sub.8 is a C.sub.1 -C.sub.4 alkyl, --COR.sub.9, --CONR.sub.9 R.sub.10 or --NR.sub.9 R.sub.10 where R.sub.9 and R.sub.10 are each hydrogen or C.sub.1 -C.sub.4 alkyl;
- R.sub.3 is nitrile, carboxy or --COOR.sub.11 where R.sub.11 is a C.sub.1 -C.sub.4 alkyl;
- and
- R.sub.4 is --NR.sub.12 R.sub.13, --NR.sub.12 COR.sub.13, --N(COR.sub.12).sub.2, --N.dbd.CHOCH.sub.2 R.sub.12, ##STR16## or 1-pyrrolyl;
- wherein R.sub.12 and R.sub.13 are each hydrogen or C.sub.1 -C.sub.4 alkyl;
- X is C.sub.2 -C.sub.4 alkylene;
- wherein 1-pyrrolyl is optionally substituted with one or two moieties selected from the group consisting of C.sub.1 -C.sub.4 alkyl, carboxy, hydroxy-C.sub.1 -C.sub.4 alkyl, or --CHO;
- or a pharmaceutically-acceptable salt thereof.
7 more elements
Dependencies are inferred from the claim text.