Back to results
US 5,332,820 AGranted
Dibenzobicyclo(2.2.2) octane angiotensin II antagonists
AssigneeE. I. Du Pont de Nemours and Company
InventorJohn J. V. Duncia
Life of this patent
Estimating the term…
Abstract
Novel substituted dibenzobicyclo[2.2.2]octanes of formula I, which are useful as angiotensin II antagonists, are disclosed: ##STR1##
Claims10
A compound of formula I:
- ##STR128## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently --H, --COOH, --CONHOR.sup.14 ;
- --CONHNHSO.sub.2 CF.sub.3 ;
- --NHSO.sub.2 CF.sub.3 ;
- --CH.sub.2 NHSO.sub.2 CF.sub.3 ;
- ##STR129## alkyl of 1 to 5 carbon atoms;
- perfluoroalkyl of 1 to 5 carbon atoms;
- CN, --CO.sub.2 R.sup.15, phenyl;
- or where R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 are taken together to form an aliphatic ring of 3 to 6 carbon atoms;
- provided that at least one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is always an acidic group defined by --COOH, --CONHOR.sup.14 ;
- --CONHNHSO.sub.2 CF.sub.3 ;
- --NHSO.sub.2 CF.sub.3 ;
- --CH.sub.2 NHSO.sub.2 CF.sub.3 ;
- ##STR130## and further provided that if Z, X and Y are not all N then at least one of R.sup.1 -R.sup.4 or R.sup.10 -R.sup.13 is always a tetrazolyl group as defined by ##STR131## R.sup.5 and R.sup.6 are independently H, CH.sub.3, Cl, Br, I, F, --OCH.sub.3, --OCOCH.sub.3 ;
- R.sup.7 is H, F, Cl, Br, I, NO.sub.2, perfluoroalkyl of 1 to 5 carbon atoms;
- CN;
- COR.sup.17 ;
- straight or branched alkyl of 1 to 6 carbon atoms;
- phenyl;
- phenylthio;
- alkenyl of 2 to 10 carbon atoms;
- alkynyl of 2 to 10 carbon atoms;
- phenylalkenyl where the alkenyl portion is 2 to 6 carbon atoms;
- phenylalkynyl where the alkynyl portion is 2 to 6 carbon atoms;
- heteroaryl selected from 2- and 3-thienyl, 2- and 3-furyl, and substituted phenyl, phenylalkenyl, phenylalkynyl, and heteroaryl selected from 2- and 3-thienyl, 2- and 3-furyl substituted with one or two substituents selected from halogen, alkoxy of 1 to 5 carbon atoms, alkyl of 1 to 5 carbon atoms, --NO.sub.2, --CN, --CF.sub.3, --COR.sup.15, --CH.sub.2 OR.sup.18, and --NHCOR.sup.18 where R.sup.18 is other than H;
- 1- or 2-naphthyl;
- 2-, 3-, 4-, 5-, 6-, or 7-benzofuryl, unsubstituted or substituted with one or two substituents selected from halogen, alkoxy of 1 to 5 carbon atoms, alkyl or 1 to 5 carbon atoms, --NO.sub.2, --CN, --CF.sub.3, --COR.sup.15, --CH.sub.2 OR.sup.18, and --NHCOR.sup.18 where R.sup.18 is other than H;
- R.sup.8 is H;
- CN;
- COR.sup.17 ;
- --(CH.sub.2).sub.n-1 CH(OR.sup.18)R.sup.19 ;
- --(CH.sub.2).sub.n O(CO)R.sup.18 where R.sup.18 is other than H;
- --(CH.sub.2).sub.n COR.sup.17 ;
- R.sup.9 is alkyl of 2 to 6 carbon atoms;
- alkenyl or alkynyl of 2 to 6 carbon atoms;
- cycloalkyl of 3 to 8 carbon atoms;
- cycloalkylalkyl of 4 to 8 carbon atoms;
- alkylthio where the alkyl portion is of 2 to 5 carbon atoms;
- R.sup.10, R.sup.11, R.sup.12, R.sup.13 are independently H, Cl, Br, I, F, NO.sub.2, CN, OH, alkyl of 1 to 4 carbon atoms;
- alkylcarbonyloxy of 1 to 4 carbon atoms;
- alkoxy of 1 to 4 carbon atoms;
- --CO.sub.2 H;
- --CO.sub.2 R.sup.15 ;
- --NHSO.sub.2 CF.sub.3 ;
- --CONHOR.sup.14 ;
- phenyl;
- ##STR132## R.sup.14 is H, methyl or benzyl;
- R.sup.15 is H;
- alkyl of 1 to 5 carbon atoms;
- branched alkyl of 1 to 5 carbon atoms;
- phenyl;
- R.sup.16 is CN, NO.sub.2 or CO.sub.2 R.sup.15 ;
- R.sup.17 is H, alkyl of 1 to 6 carbon atoms;
- --OR.sup.15, --NR.sup.18 R.sup.19 ;
- R.sup.18 and R.sup.19 are independently H, alkyl of 1 to 5 carbon atoms;
- phenyl;
- R.sup.20 and R.sup.21 are independently --H;
- Cl;
- Br;
- I;
- --SR.sup.15 ;
- --R.sup.17 ;
- --CN;
- --OR.sup.15 ;
- phenyl;
- substituted phenyl where the substituents are alkoxy of 1 to 5 carbon atoms, alkyl of 1 to 5 carbon atoms, fluorine;
- Z is N;
- CH;
- X is C-R.sup.7 ;
- C-R.sup.8 ;
- N;
- Y is C-R.sup.8 ;
- C-R.sup.7 ;
- N;
- X and Y are carbon atoms and Z is N when they are part of the following ring system;
- ##STR133## V is CH or N when W is CH;
- W is CH or N when V is CH;
- m is 1,2;
- n is 1-5.
75 more elements
Dependencies are inferred from the claim text.