Claims
- 1. A compound of the formula ##STR55## wherein Ar represents a phenyl or naphthyl group which may be unsubstituted or substituted with lower alkyl from 1 to 6 carbon atoms, alkenyl of from 1 to 6 carbon atoms, alkynyl of from 2 to 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 6 carbon atoms, halogen, acetamido, amino, nitro, phenoxy, alkylamino of from 1 to 10 carbon atoms, hydroxy, hydroxyalkyl of from 1 to 10 carbon atoms, cyano, arylalkoxy wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents phenyl which may be unsubstituted or substituted with lower alkyl from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 6 carbon atoms, halogen, acetamido, amino, nitro, phenoxy, alkylamino of from 1 to 10 carbon atoms, hydroxy, hydroxyalkyl of from 1 to 10 carbon atoms, cyano; W represents alkylene of from 1 to 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, phenyl or aralkyl wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents phenyl which may be unsubstituted or substituted with lower alkyl from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 6 carbon atoms, halogen, acetamido, amino, nitro, phenoxy, alkylamino of from 1 to 10 carbon atoms, hydroxy, hydroxyalkyl of from 1 to 10 carbon atoms, cyano, arylalkoxy wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents phenyl; 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 and R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; and except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 2. A compound of the formula ##STR56## wherein Ar represents phenyl or naphthyl group which may be unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 6 carbons atoms, halogen, acetamido, amino, nitro, alkylamino of from 1 to 6 carbon atoms, hydroxy, hydroxyalkyl of from 1 to 6 carbon atoms, cyano or arylalkoxy wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group is substituted or unsubstituted phenyl; W represents alkylene of from 1 to 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, OR --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 6 carbon atoms, phenyl which may be unsubstituted or substituted with alkyl of 1 to 6 carbon atoms; 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; aralkyl wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents phenyl unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms; and except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 3. A compound of the formula ##STR57## wherein Ar represents phenyl which is unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms, halogen, hydroxy, nitro, amino, phenoxy, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, a phenyl group which may be unsubstituted or substituted with lower alkyl of from 1 to 10 carbon atoms, alkenyl of from 2 to 10 carbon atoms, alkynyl of from 2 to 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 10 carbon atoms, halogen, acetamido, amino, nitro, alkylamino of from 1 to 10 carbon atoms, hydroxy, hydroxyalkyl of from 1 to 10 carbon atoms, cyano, arylalkoxy wherein the alkyl group contains from 1 to 6 carbon atoms; or 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 4. A compound of the formula ##STR58## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, hydroxyalkyl of from 1 to 6 carbon atoms, nitro, amino, alkyl of from 1 to 6 carbon atoms, phenoxy, benzyloxy, or alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms; W represents alkylene of from 1 to 6 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R1--NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2, and R.sub.3 may be the same or different and represent, hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, phenyl, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 5. A compound according to claim 1 of the formula ##STR59## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, hydroxyalkyl of from 1 to 6 carbon atoms, nitro, amino, benzyloxy, phenoxy, alkyl containing from 1 to 6 carbon atoms, or alkoxy wherein the alkyl group contains from 1 to 6 carbon atoms; W represents alkylene of from 1 to 6 carbon atoms; and Y is --COR.sub.1, --CONR.sub.1 R.sub.3, --SO.sub.2 R.sub.1, --SO.sub.2 NR.sub.1 R.sub.3, or --COOR.sub.1, wherein R.sub.1 and R.sub.3 may be the same or different and may be hydrogen, alkyl containing from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, phenyl, which may be unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms, halogen, hydroxy, nitro, amino, phenoxy, benzyloxy, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; aralkyl wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents phenyl which may be unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms, halogen, hydroxy, nitro, amino, phenoxy, or benzyloxy with the proviso that at least one of R.sub.1 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; and except that R.sub.1 is not hydrogen when Y is --SO.sub.2 R.sub.1 or --COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 6. A compound according to claim 1 of the formula ##STR60## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 represents 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 7. A compound according to claim 1 of the formula ##STR61## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 4 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, phenyl, or benzyl; 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 8. A compound according to claim 1 of the formula ##STR62## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 represents 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 9. A compound according to claim 1 of the formula ##STR63## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 4 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, phenyl, benzyl, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2- or 3-indole; or a pharmaceutically acceptable salt thereof.
- 10. A compound according to claim 1 of the formula ##STR64## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 represents 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 11. A method for the treatment or prophylaxis of cardiac disorders in a mammal comprising administering to such animal a short-acting beta-blocking compound of the formula ##STR65## wherein Ar represents phenyl or naphthyl group which may be unsubstituted or substituted with lower alkyl of from 1 to 10 carbon atoms, alkenyl of from 2 to 10 carbon atoms, alkynyl of from 2 to 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 10 carbon atoms, halogen, acetamido, amino, nitro, alkylamino of from 1 to 10 carbon atoms, hydroxy, hydroxyalkyl of from 1 to 10 carbon atoms, cyano, arylalkoxy wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents substituted or unsubstituted phenyl and groups of the formula ##STR66## wherein R.sub.4 is lower alkyl, aryl or aralkyl and A is a direct bond, alkylene of from 1 to 10 carbon atoms or alkenylene of from 2 to 10 carbon atoms; W represents alkylene of from 1 to 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, aryl, or aralkyl wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents phenyl, benzyl, phenethyl 3,4-dimethoxyphenethyl; or 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub. 1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; and except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or a pharmaceutically acceptable salt thereof.
- 12. The method of claim 11 wherein the compound is of the formula ##STR67## wherein Ar represents an aromatic group which may be unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 6 carbon atoms, halogen, acetamido, amino, nitro, alkylamino of from 1 to 6 carbon atoms, hydroxy, hydroxyalkyl of from 1 to 6 carbon atoms, cyano or arylalkoxy wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group is phenyl; which may be unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms, halogen, hydroxy, nitro, amino, phenoxy, or benzyloxy; W represents alkylene of from 1 to 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 6 carbon atoms, aralkyl wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents a substituted or unsubstituted aromatic group of from 2 to 10 carbon atoms wherein the substituent groups may be alkyl of from 1 to 6 carbon atoms; phenyl, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 13. The method of claim 11 wherein the compound is of the formula ##STR68## wherein Ar represents phenyl which is unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms, halogen, hydroxy, nitro, amino, phenoxy, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1, wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, a substituted or unsubstituted aryl group of from 5 to 6 carbon atoms wherein the substituent group may be alkyl of from 1 to 6 carbon atoms; 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-imdole; except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 14. The method of claim 11 wherein the compound is of the formula ##STR69## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, hydroxyalkyl of from 1 to 6 carbon atoms, nitro, amino, alkyl of from 1 to 6 carbon atoms, phenoxy, benzyloxy, or alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms; W represents alkylene of from 1 to 6 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2, and R.sub.3 may be the same or different and represent, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, phenyl, benzyl, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 15. The method of claim 11 wherein the compound is of the formula ##STR70## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, hydroxyalkyl of from 1 to 6 carbon atoms, nitro, amino, benzyloxy, phenoxy, alkyl containing from 1 to 6 carbon atoms, or alkoxy wherein the alkyl group contains from 1 to 6 carbon atoms; W represents ethylene, 1-methylene, or 1,1-dimethylethylene, and Y is --COR.sub.1, --CONR.sub.1 R.sub.3, --SO.sub.2 R.sub.1, --SO.sub.2 NR.sub.1 R.sub.3, or --COOR.sub.1, wherein R.sub.1 and R.sub.3 may be the same or different and may be hydrogen, alkyl containing from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, phenyl, which may be unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms, halogen, hydroxy, nitro, amino, phenoxy, or benzyloxy; aralkyl wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents substituted or unsubstituted phenyl or a benzyl, phenethyl, 3,4-dimethoxyphenethyl group; or 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when Y is --SO.sub.2 R.sub.1 or --COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 16. The method of claim 11 wherein the compound is of the formula ##STR71## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 17. The method of claim 11 wherein the compound is of the formula ##STR72## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 4 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, phenyl, or benzyl, 1 or 2-thiophenyd, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 18. The method of claim 11 wherein the compound is of the formula ##STR73## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 represents 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 19. The method of claim 11 wherein the compound is of the formula ##STR74## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 4 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, phenyl, benzyl, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 20. The method of claim 11 wherein the compound is of the formula ##STR75## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 represents 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 21. A method according to claim 11 wherein the compound is administered parenterally.
- 22. A method according to claim 21 wherein the compound is administered by intravenous injection or intravenous infusion at a dosage rate of from 0.001 to about 100 mg. of compound per kg. of body weight of said mammal per hour.
- 23. A method of treating glaucoma or lowering intraocular pressure in a mammal, which comprises topically applying to the eye of said mammal an intraocular pressure-lowering effective amount of a compound of the formula ##STR76## wherein Ar represents a phenyl or naphthyl group which may be unsubstituted or substituted with lower alkyl of from 1 to 10 carbon atoms, alkenyl of from 2 to 10 carbon atoms, alkynyl of from 2 to 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 10 carbon atoms, halogen, acetamido, amino, nitro, alkylamino, of from 1 to 10 carbon atoms, hydroxy, hydroxyalkyl of from 1 to 10 carbon atoms, cyano, arylalkoxy wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents substituted or unsubstituted phenyl; W represents alkylene of from 1 to 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, aryl, or aralkyl, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 24. The method of claim 23 wherein the compound is of the formula ##STR77## wherein Ar represents an aromatic group which may be unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 6 carbon atoms, halogen, acetamido, amino, nitro, alkylamino of from 1 to 6 carbon atoms, hydroxy, hydroxyalkyl of from 1 to 6 carbon atoms, cyano or arylalkoxy wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group is phenyl which may be unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms, halogen, hydroxy, nitro, amino, phenoxy or benzyloxy; W represents alkylene of from 1 to 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1 , --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 6 carbon atoms, aralkyl wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents phenyl, benzyl, phenethyl, or 3,4-dimethoxyphenethyl; 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 25. The method of claim 23 wherein the compound is of the formula ##STR78## wherein Ar represents phenyl which is unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 4 carbon toms, halogen, hydroxy, nitro, amino, phenoxy, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1, wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, a substituted or unsubstituted aryl group of from 5 to 6 carbon atoms wherein the substituent groups may be alkyl of from 1 to 6 carbon atoms; 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 26. The method of claim 23 wherein the compound is of the formula ##STR79## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, hydroxyalkyl of from 1 to 6 carbon atoms, nitro, amino, alkyl of from 1 to 6 carbon atoms, phenoxy benzyloxy, or alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms; W represents alkylene of from 1 to 6 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2, and R.sub.3 may be the same or different and represent alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, phenyl, benzyl, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or a pharmaceutically acceptable salt thereof.
- 27. The method of claim 23 wherein the compound is of the formula ##STR80## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, hydroxyalkyl of from 1 to 6 carbon atoms, nitro, amino, benzyloxy, phenoxy, alkyl containing from 1 to 6 carbon atoms, or alkoxy wherein the alkyl group contains from 1 to 6 carbon atoms; W represents ethylene, 1-methylethylene, or 1,1-dimethylethylene, and Y is --COR.sub.1, --CONR.sub.1 R.sub.3, --SO.sub.2 R.sub.1, --SO.sub.2 NR.sub.1 R.sub.3, or --COOR.sub.1, wherein R.sub.1 and R.sub.3 may be the same or different and may be hydrogen, alkyl containing from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, phenyl, which may be unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms, halogen, hydroxy, nitro, amino, phenoxy, or benzyloxy; aralkyl wherein the alkyl group contains from 1 to 6 carbon atoms and the aryl group represents phenyl which may be unsubstituted or substituted with alkyl of from 1 to 6 carbon atoms, alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms, halogen, hydroxy, nitro, amino, phenoxy; or 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when Y is --SO.sub.2 R.sub.1 or --COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
- 28. The method of claim 23 wherein the compound is of the formula ##STR81## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 represents 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or - 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 29. The method of claim 23 wherein the compound is of the formula ##STR82## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 4 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, phenyl, or benzyl, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 30. The method of claim 23 wherein the compound is of the formula ##STR83## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 represents 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pyrrolidine, piperidine, piperazine, morpholine or thiomorpholine ring, or a pharmaceutically acceptable salt thereof.
- 31. The method of claim 23 wherein the compound is of the formula ##STR84## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 4 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, phenyl, benzyl, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 32. The method of claim 23 wherein the compound is of the formula ##STR85## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, nitro, amino, alkyl of from 1 to 4 carbon atoms, or benzyloxy; W represents alkylene of from 1 to 6 carbon atoms; and R.sub.1 represents 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; or a pharmaceutically acceptable salt thereof.
- 33. A method for the treatment or prophylaxis of cardiac disorders comprising administering to a patient in need of such treatment a therapeutically effective amount of a beta-blocking compound of the formula ##STR86## wherein X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent hydrogen, halogen, hydroxy, hydroxyalkyl of from 1 to 6 carbon atoms, nitro, amino, alkyl of from 1 to 6 carbon atoms, phenoxy, benzyloxy, or alkoxy wherein the alkyl group contains from 1 to 4 carbon atoms; W represents alkylene of from 1 to 6 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2, and R.sub.3 may be the same or different and represent hydrogen, alkyl of from 1 to 6 carbon atoms, alkoxyalkyl wherein the alkyl groups may be the same or different and contain from 1 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, phenyl or benzyl, 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 is 1 or 2-thiophenyl, 2, 4 or 5-imidazole, 1- 2- or 1- 3-oxazole or 2 or 3-indole; except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1 ; or a pharmaceutically acceptable salt thereof.
Parent Case Info
This application is a division of application Ser. No. 320,773, filed Nov. 12, 1981, now U.S. Pat. No. 4,582,855.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4333946 |
Durant et al. |
Jun 1982 |
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Divisions (1)
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Number |
Date |
Country |
Parent |
320773 |
Nov 1981 |
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