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US 5,877,196 AGranted
N-4-(imidazolyl or pyrazolyl)phenyl(oxy, sulfinyl, sulfenyl or sulfonyl)alkyl!carboxamides, sulfonamides or phosphoramides having antiarrhythmic properties
AssigneeAmerican Cyanamid Company
InventorsAndrew Stephen Tomcufcik, Joseph William Hinson
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Abstract
The present invention relates to substituted .omega.-phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl! alkyl, alkenyl or alkynyl!amine carboxamides, sulfonamides and phosphonylamides which are useful as antiarrhythmic agents.
Claims9
A compound according to Formula I:
- ##STR26## wherein R.sup.1 is ##STR27## X is O, S, SO, or SO.sub.2 ;
- D is --(CH.sub.2).sub.n --, cis or trans --(CH.sub.2).sub.k --CH.dbd.CH--(CH.sub.2).sub.m --, or --(CH.sub.2).sub.k --C.tbd.C--(CH.sub.2).sub.m --, where n is 3-10, m is 1-4, and k is 1-4;
- Y is C(.dbd.O)R.sup.2 or SO.sub.2 R.sup.2 ;
- R.sup.2 is ##STR28## Z, Z.sup.1 and Z.sup.2 are independently selected from H, C.sub.1 -C.sub.4 straight or branched alkyl, --CF.sub.3, --NO.sub.2, --NHCOR.sup.3, --OR.sup.4, --CN, Cl, Br, F, or I;
- R.sup.3 is C.sub.1 -C.sub.3 straight chain alkyl;
- and
- R.sup.4 is a C.sub.1-C.sub.4 straight or branched alkyl;
- with the provisos that when R.sup.1 is 1-imidazolyl, X is oxygen, D is --(CH.sub.2).sub.4 --, Y is --C(.dbd.O)R.sup.2, R.sup.2 is ##STR29## and two of Z, Z.sup.1 and Z.sup.2 are H, then the remaining substituent Z, Z.sup.1, or Z.sup.2 cannot be Cl in the 4-position;
- and
- when R.sup.1 is 1-imidazolyl, D is --(CH.sub.2).sub.n --Y is --SO.sub.2 R.sup.2 and R.sup.2 is ##STR30## at least one of Z, Z.sup.1 and Z.sup.2 is selected from CF.sub.3, --NO.sub.2,--NHCOR.sup.3, and --CN;
- or a pharmaceutically acceptable salt thereof.
8 more elements
A method of treating cardiac arrhythmias in a mammal which comprises administering to a mammal having a cardiac arrhythrnia a therapeutically effective amount of a compound according to Formula I:
- ##STR31## wherein R.sup.1 is ##STR32## X is O, S, SO, or SO.sub.2 ;
- D is --(CH.sub.2).sub.n --, cis or trans --(CH.sub.2).sub.k --CH.dbd.CH--(CH.sub.2).sub.m --, or --(CH.sub.2).sub.k --C.tbd.C--(CH.sub.2).sub.m --, where n is 3-10, m is 1-4, and k is 1-4;
- Y is C(.dbd.O)--R.sup.2 or SO.sub.2 R.sup.2 ;
- R.sup.2 is ##STR33## Z, Z.sup.1 and Z.sup.2 are independently selected from H, C.sub.1 -C.sub.4 straight or branched alkyl, --CF.sub.3, --NO.sub.2, --NHCOR.sup.3, --OR.sup.4, --CN, Cl, Br, F, or I;
- R.sup.3 is C.sub.1 -C.sub.3 straight chain alkyl;
- and
- R.sup.4 is a C.sub.1 -C.sub.4 straight or branched alkyl;
- with the proviso that when R.sup.1 is 1-imidazolyl, X is oxygen, D is --(CH.sub.2).sub.4 --, Y is C(.dbd.O)R.sup.2, R.sup.2 is ##STR34## and two of Z, Z.sup.1 and Z.sup.2 are H, then the remaining substituent Z, Z.sup.1, or Z.sup.2 cannot be Cl in the 4-position;
- or a pharmaceutically acceptable salt thereof.
6 more elements
Dependencies are inferred from the claim text.