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US 4,680,299 AGranted
2-phenyl-4-quinolinecarboxylic acids and pharmaceutical compositions thereof
AssigneeE.I. du Pont de Nemours and Company
InventorDavid P. Hesson
Life of this patent
Estimating the term…
Abstract
Phenylquinolinecarboxylic acids and derivatives thereof, such as 2-(2'-fluoro-1,1'-biphenyl-4-yl)-6-fluoro-3-methyl-4-quinolinecarboxylic acid, or a sodium or potassium salt thereof, are useful as tumor inhibiting agents.
Claims22
A compound having the formula:
- ##STR37## wherein ##STR38## R.sup.1 is cyclohexyl, ##STR39## when R is ##STR40## R.sup.1 can be in addition alkyl of 3-4 carbon atoms;
- R.sup.2 is ##STR41## R.sup.3 is H, alkoxy of 1-3 carbon atoms, or alkyl of 1-2 carbon atoms;
- R.sup.4 is CO.sub.2 H or CO.sub.2 R.sup.11 ;
- R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are independently H, F, Cl, Br, I, CH.sub.3, CF.sub.3, SCH.sub.3 or CH.sub.2 CH.sub.3, at least two of R.sup.5, R.sup.6, R.sup.7, and R.sup.8 being H;
- R.sup.9 and R.sup.9A are independently H or alkyl of 1 to 3 carbon atoms;
- R.sup.11 is (CH.sub.2).sub.2-4 NR.sup.9 R.sup.9A ;
- W, Y and Z are independently H, F, Cl, Br, alkyl of 1-5 carbon atoms, NO.sub.2, OH, CF.sub.3 or OCH.sub.3 ;
- m is 0 or 1;
- or
- a pharmaceutically suitable salt thereof;
- with the following provisos:
- (1) when R.sup.4 is CO.sub.2 H, R.sup.1 is phenyl or phenoxy, and R.sup.5, R.sup.7 and R.sup.8 are H, R.sup.6 cannot be Br;
- (2) R.sup.5, R.sup.6 and R.sup.7 cannot all be H;
- (3) when R.sup.4 is CO.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2, R.sup.6 is CH.sub.2 CH.sub.3, or R.sup.7 is Cl, R.sup.1 cannot be cyclohexyl;
- (4) when R.sup.1 is cyclohexyl and R.sup.3 is H, R.sup.6 must be Cl or F, but R.sup.6 and R.sup.8 cannot both be Cl;
- and
- (5) when R.sup.6 is CH.sub.3, R.sup.7 cannot be Cl.
14 more elements
A pharmaceutical composition consisting essentially of a suitable pharmaceutical carrier and at least one compound having the formula:
- ##STR42## wherein ##STR43## R.sup.1 is CH.sub.3 CH.sub.2 (CH.sub.3)CH, alkyl of 5-12 carbon atoms, cyclohexyl, ##STR44## when R is ##STR45## R.sup.1 can be in addition alkyl of 3-4 carbon atoms;
- R.sup.2 is ##STR46## R.sup.3 is H, alkoxy of 1-3 carbon atoms, or alkyl of 1-2 carbon atoms;
- R.sup.4 is CO.sub.2 H or CO.sub.2 R.sup.11 ;
- R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are independently H, F, Cl, Br, I, CH.sub.3, CF.sub.3, SCH.sub.3 or CH.sub.2 CH.sub.3, at least two of R.sup.5, R.sup.6, R.sup.7, and R.sup.8 being H;
- R.sup.9 and R.sup.9A are independently H or alkyl of 1 to 3 carbon atoms;
- R.sup.11 is (CH.sub.2).sub.2-4 NR.sup.9 R.sup.9A ;
- W, Y and Z are independently H, F, Cl, Br, alkyl of 1-5 carbon atoms, NO.sub.2, OH, CF.sub.3 or OCH.sub.3 ;
- m is 0 or 1;
- or
- a pharmaceutically suitable salt thereof;
- with the following provisos:
- (1) R.sup.5, R.sup.6 and R.sup.7 cannot all be H;
- (2) when R.sup.4 is CO.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2, R.sup.6 is CH.sub.2 CH.sub.3, or R.sup.7 is Cl, R.sup.1 cannot be cyclohexyl;
- (3) when R.sup.1 is cyclohexyl and R.sup.3 is H, R.sup.6 must be Cl or F, but R.sup.6 and R.sup.8 cannot both be Cl;
- and
- (4) when R.sup.6 is CH.sub.3, then R.sup.7 cannot be Cl.
13 more elements
A pharmaceutical composition consisting essentially of a suitable pharmaceutical carrier and at least one compound having the formula:
- ##STR47## wherein R.sup.1 is cyclohexyl;
- phenyl;
- phenyl substituted with one halogen;
- alkyl of 1-5 carbon atoms or CF.sub.3 ;
- phenoxy;
- or phenoxy substituted with one halogen or alkyl of 1-5 carbon atoms;
- R.sup.3 is H or alkyl of 1-2 carbon atoms;
- R.sup.4 is CO.sub.2 H, a sodium or potassium salt theeof, or CO.sub.2 R.sup.11 ;
- R.sup.5 and R.sup.6 are independently H, halogen, CH.sub.3 or CF.sub.3 ;
- R.sup.7 and R.sup.8 are independently H or halogen;
- R.sup.11 is (CH.sub.2).sub.2-4 NR.sup.9 R.sup.9A ;
- and
- R.sup.9 and R.sup.9A are independently alkyl of 1 to 3 carbon atoms,
- or a pharmaceutically suitable salt thereof;
- provided that R.sup.5, R.sup.6 and R.sup.7 cannot all be H and that when R.sup.1 is cyclohexyl and R.sup.3 is H, R.sup.6 must be Cl or F, but R.sup.6 and R.sup.8 cannot both be Cl, and when R.sup.6 is CH.sub.3, then R.sup.7 cannot be Cl.
12 more elements
A compound having the formula:
- ##STR48## wherein R.sup.1 is cyclohexyl, ##STR49## R.sup.3 is H or alkyl of 1-2 carbon atoms;
- R.sup.4 is CO.sub.2 H, a sodium or potassium salt thereof, or CO.sub.2 R.sup.11 ;
- R.sup.5 and R.sup.6 are independently H, halogen or CF.sub.3 provided that both R.sup.5 and R.sup.6 are not hydrogen;
- R.sup.11 is (CH.sub.2).sub.2-4 NR.sup.9 R.sup.9A ;
- R.sup.9 and R.sup.9A are independently alkyl of 1 to 3 carbon atoms;
- and
- W and Z are independently H, halogen, alkyl of 1-5 carbon atoms or CF.sub.3 ;
- provided that when R.sup.1 is phenyl or phenoxy, and R.sup.5 is H, then R.sup.6 cannot be Br;
- and that when R.sup.1 is cyclohexyl and R.sup.3 is H, R.sup.6 must be Cl or F.
6 more elements
Dependencies are inferred from the claim text.