Benzopyran-containing compounds and method for their use
AssigneeEndorecherche, Inc.
InventorsFernand Labrie, Yves Merand, Sylvain Gauthier
Life of this patent
Estimating the term…
Abstract
Certain benzopyran antiestrogens are disclosed for treating estrogen sensitive diseases such as breast cancer. Prodrug forms provide ease of manufacturing, good shelf life, and bioavailability, and preferred stereoisomers are shown to be more effective than racemic mixtures.
Claims84
An optically active compound or pharmaceutically acceptable salt thereof, said compound having the molecular structure:
- ##STR24## wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydroxyl and a moiety convertible in vivo to hydroxyl;
- wherein R.sup.3 is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --;
- and
- wherein stereoisomers that have the following absolute configuration:
- ##STR25## are present in an amount higher than 50% by weight relative to all stereoisomers present.
A compound of the following molecular structure:
- at a purity such that any 2R-stereoisomer thereof that may be present as an impurity is present at less than 10% by weight relative to all stereoisomers.
A compound or pharmaceutically acceptable further salt thereof, said compound having the molecular structure:
- ##STR28## wherein A- is an anion of a pharmaceutically acceptable acid;
- wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydroxyl and a moiety convertible in vivo to hydroxyl;
- and
- wherein R.sup.3 is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --.
A compound or pharmaceutically acceptable salt thereof, having the molecular structure:
- wherein R.sup.3 is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --;
- and
- wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydroxy, alicyclic or branched aliphatic acyloxy, and ##STR32## wherein R.sup.7 is selected from the group consisting of amino, alkylamino, aminoalkyl, alkylsulfanyl, alkoxy, alkenyloxy and alkynyloxy;
- wherein at least one of R.sup.1 or R.sup.2 is not hydroxy.
A pharmaceutical composition comprising a therapeutically acceptable amount of an optically active compound or pharmaceutically acceptable salt thereof, said compound having the molecular structure:
- ##STR34## wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydroxyl and a moiety convertible in vivo to hydroxyl;
- wherein R.sup.3 is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --;
- and
- wherein stereoisomers that have the following absolute configuration:
- ##STR35## are present in an amount higher than 50% by weight relative to all stereoisomers present.
A pharmaceutical composition comprising a pharmaceutically acceptable diluent or carrier and a therapeutically acceptable amount of a compound of the following molecular structure:
- at a purity such that any 2R-stereoisomer thereof that may be present as an impurity is present at less than 10% by weight relative to all stereoisomers.
A pharmaceutical composition comprising a pharmaceutically acceptable diluent or carrier and a therapeutically acceptable amount of a compound or pharmaceutically acceptable further salt thereof, said compound having the molecular structure:
- ##STR38## wherein A- is an anion of a pharmaceutically acceptable acid;
- where in R.sup.1 and R.sup.2 are independently selected from the group consisting of hydroxyl and a moiety convertible in vivo to hydroxyl;
- and
- wherein R.sup.3 is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --.
A pharmaceutical composition comprising a pharmaceutically acceptable diluent or carrier and a therapeutically acceptable amount of a compound or pharmaceutically effective salt thereof, having the molecular structure:
- wherein R.sup.3 is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --;
- and
- wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydroxy, acicyclic or branched aliphatic acyloxy, and ##STR42## wherein R.sup.7 is selected from the group consisting of amino, alkylamino, aminoalkyl, alkylsulfanyl, alkoxy, alkenyloxy and alkynyloxy;
- wherein at least one of R.sup.1 or R.sup.2 is not hydroxy.
Dependencies are inferred from the claim text.