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US 5,401,848 AGranted
Indane and quinoline derivatives
AssigneeE. R. Squibb & Sons, Inc.
InventorKarnail Atwal
Life of this patent
Estimating the term…
Abstract
Novel indane and quinoline derivatives, useful, for example, as antiischemic agents, having the formula ##STR1## where A, X, R.sub.1 -R.sub.7 are as defined herein, are disclosed.
Claims11
A compound having the formula ##STR17## wherein X is NCN;
- and A is a single bond or NR.sub.9 wherein R.sub.9 is alkyl of 1-4 carbons;
- Y is --NR.sub.8 ;
- R.sub.1 is aryl or arylalkyl;
- R.sub.2 is hydrogen, hydroxy, or ##STR18## R.sub.3 and R.sub.4 are each independently hydrogen, alkyl or arylalkyl;
- R.sub.5 is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, arylalkyl, cycloalkylalkyl, --CN, --NO.sub.2, --COR, --COOR, --CONHR, --CONR.sub.2, --CF.sub.3, S-alkyl, --SOalkyl, --SO.sub.2 alkyl, ##STR19## halogen, OCF.sub.3, OCH.sub.2 CF.sub.3, wherein R in each of the above groups is hydrogen, alkyl, aryl, arylalkyl, cycloalkyl, (cycloalkyl)alkyl or haloalkyl;
- R.sub.6 is hydrogen, alkyl, halo, OH, O-alkyl, amino and substituted amino, as defined hereinbelow, O-alkyl, --OCOalkyl, --OCONRalkyl, --NRCOalkyl, and NRCOOalkyl, NRCONR.sub.2 wherein R in each of the above groups is hydrogen, alkyl, aryl, arylalkyl, cycloalkyl, (cycloalkyl)alkyl or haloalkyl;
- R.sub.7 and R.sub.8 are each independently hydrogen, alkyl, or arylaklyl;
- or R.sub.1 and R.sub.8, or R.sub.1 and R.sub.7 or R.sub.7 and R.sub.8 taken together can form a 5- to 7-membered ring, which may further include an aryl group fused to 2 carbon atoms of such 5- to 7-membered ring;
- n is 1, 2 or 3;
- and,
- R.sub.10 is hydrogen, hydroxy, alkyl or O-alkyl;
- and further wherein
- the term "alkyl" refers to straight or branched chain saturated hydrocarbon radicals having up to eight carbons;
- the terms "alkoxy" and "alkylthio" refer to such alkyl groups attached to an oxygen or sulfur;
- the term "alkenyl" refers to straight or branched chain hydrocarbon radicals having from two to eight carbons and one double bond;
- the term "alkynyl" refers to straight or branched chain hydrocarbon radicals having from two to eight carbons and one triple bond;
- the term "cycloalkyl" refers to saturated carbocyclic rings of 3 to 7 carbon atoms;
- the term "halo" or "halogen" refers to chloro, bromo, iodo and fluoro;
- the term "halo substituted alkyl" refers to such alkyl groups described above in which one or more hydrogens have been replaced by chloro, bromo or fluoro groups;
- the term "aryl" refers to phenyl, 1-naphthyl, 2-naphthyl or mono substituted phenyl, 1-naphthyl, 2-naphthyl wherein said substituent is alkyl of 1 to 4 carbons, alkylthio of 1 to 4 carbons, alkoxy of 1 to 4 carbons, halo, nitro, cyano hydroxy, amino, --NH-alkyl wherein alkyl is of 1 to 4 carbons, --N(alkyl).sub.2 wherein alkyl is of 1 to 4 carbons, N(R.sub.11)COR.sub.11 ', N(R.sub.11)CO-haloalkyl, N(R.sub.11)CO-amino, N(R.sub.11)CO-substituted amino, COR.sub.11, COOR.sub.11 (wherein R.sub.11 and R.sub.11 ' are independently H, alkyl, haloalkyl, aryl, arylalkyl) --CF.sub.3, --OCHF.sub.2, ##STR20## (wherein R.sub.12 is hydrogen, alkyl of 1 to 4 carbons, alkoxy of 1 to 4 carbons, alkylthio of 1 to 4 carbons, halo, hydroxy or CF.sub.3), --O--CH.sub.2 -cycloalkyl, or --S--CH.sub.2 - cycloalkyl, and di-substituted phenyl, 1-naphthyl, 2-naphthyl wherein said substituents are selected from methyl, methoxy, methylthio, halo, CF.sub.3, nitro, amino, and OCHF.sub.2 ;
- the term "substituted amino" refers to a group of the formula --NZ.sub.1 Z.sub.2 wherein Z.sub.1 is hydrogen, alkyl, cycloalkyl, aryl, arylalkyl or cycloalkylalkyl and Z.sub.2 is alkyl, cycloalkyl, aryl, arylalkyl or cycloalkylalkyl.
18 more elements
Dependencies are inferred from the claim text.