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US 5,393,768 AGranted
Leukotriene antagonists
AssigneeEli Lilly and Company
InventorRobert D. Dillard
Life of this patent
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Abstract
This invention provides novel benzene derivatives which are leukotriene antagonists, formulations of those derivatives, intermediates for preparing the derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.
Claims18
A compound of the formula I ##STR51## or a pharmaceutically acceptable salt thereof, wherein:
- R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl, phenyl-substituted-(C.sub.1 -C.sub.3 alkyl), phenyl, or phenyl substituted with halo, C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.4 alkoxy;
- R.sub.2 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.6 alkenyl, benzyl, or 2-phenylethyl;
- R.sub.3 is hydrogen, bromo, or chloro;
- Z is ##STR52## m is 0-4;
- A is a bond, ##STR53## Q is a bond, ##STR54## and R.sub.4 is ##STR55## where each of R, R', and R" is independently hydrogen or C.sub.1 -C.sub.3 alkyl;
- each of R.sub.5 and R.sub.6 is independently hydrogen, C.sub.1 -C.sub.3 ;
- alkyl, phenyl, or benzyl;
- R.sub.9 is hydroxy, C.sub.1 -C.sub.4 alkoxy, --NHOH, or --NR.sub.14 R.sub.15 ;
- R.sub.10 is hydrogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, halo, C.sub.1 -C.sub.4 alkyl, amino, mono-or di-(C.sub.1 -C.sub.3 alkyl) amino, or (C.sub.1 -C.sub.3 alkyl)CONH--;
- R.sub.11 is ##STR56## R.sub.12 is hydrogen or C.sub.1 -C.sub.3 alkyl;
- R.sub.13 is hydrogen or methyl;
- each of R.sub.14 and R.sub.15 is independently hydrogen, C.sub.1 -C.sub.3 alkyl, or when taken together with the nitrogen/atom form a morpholine or N-methyl piperazine ring;
- R is 0-4;
- s is 1-4;
- W is a bond, --O--, --NR'"--, or ##STR57## R'" is hydrogen or C.sub.1 -C.sub.3 alkyl;
- and p is 0, 1, or 2;
- provided that
- (a) when R.sub.4 is --COR.sub.9, hydroxy, --NR.sub.11 R.sub.12, or ##STR58## Q may only be a bond and n may not be 0. (b) when A is --O--, ##STR59## --NR'--, or --CHOH--, and Z is --O--, ##STR60## --NR--, m may not be 0;
- (c) when A is --O--, ##STR61## --NR'--, OR --CHOH--, and Q is --O--, ##STR62## or --NR"--, n may not be 0;
- (d) when Z is --O--, ##STR63## or --NR--, Q is --O--, ##STR64## or --NR"--, and A is a bond, m and n may not both be 0;
- and (e) if A is ##STR65## (1) when Z is ##STR66## m may not be 0, (2) when Q is ##STR67## n may not be 0;
- and (3) when Z is --O-- or --NR-- and Q is --O-- or --NR"--, m and n may not both be 0.
19 more elements
A compound of the formula ##STR70## and pharmaceutically acceptable salts thereof wherein:
- R.sub.2 ' is C.sub.1 -C.sub.6 alkyl;
- Z' is --0--, ##STR71## or --NH--;
- each of R.sub.16 ' and R.sub.17 ' are independently hydrogen or methyl;
- r' is 0, 1, or 2;
- and
- R.sub.4 ' is --COOH, 5-tetrazolyl, or 5-thiotetrazolyl.
3 more elements
4-(4-acetyl-3-hydroxy-2-propylbenzyloxy)butanoic acid or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.