Alkyl, alkoxy and thioalkoxy substituted diphenyl acetylenes having retinoid like activity
AssigneeAllergan, Inc.
InventorRoshantha A. S. Chandraratna
Life of this patent
Estimating the term…
Abstract
Retinoid like activity is exhibited by compounds of the formula ##STR1## where R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl cycloalkyl, lower alkenyl, SR* or OR* where R* is lower alkyl, cycloalkyl or lower alkenyl; Y is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl or (CH.sub.2).sub.n where n is 0-6; and Z is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR' or a ketal derivative where R' is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claims46
Compounds of the formula ##STR16## wherein R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, tertiary butyl, 4-methylpentyl, 1,1,4-trimethylpentyl, cycloalkyl, lower alkenyl, or OR.sup.* where R.sup.* is lower brach chained alkyl, cycloalkyl or lower alkenyl with the proviso that one of A and B is not hydrogen;
- Y is lower alkenyl, lower alkynyl lower cycloalkyl, lower branched chain alkyl, or (CH.sub.2).sub.n where n is 0-6;
- and
- Z is --C))H or a pharmaceutically acceptable salt, or ester thereof.
Compounds of the formula ##STR17## wherein R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR.sup.* and OR.sup.* and one of the A and B groups is SR.sup.* where R.sup.* is lower alkyl, cycloalkyl or lower alkenyl, Y is lower alkenyl, lower alkynyl lower cycloalkyl, lower branched chain alkyl, or (CH.sub.2).sub.n where n is 0-6;
- and
- Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Compounds of the formula ##STR18## wherein A and B and R.sub.1 -R.sub.4 independently are hydrogen, tertiary butyl, 4-methylpentyl, 1,1,4-trimethylpentyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is not hydrogen;
- n is 0-6;
- and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Compounds of the formula ##STR19## wherein R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, or SR.sup.* where R.sup.* is lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is SR.sup.* ;
- n is 0-6;
- and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Compounds of the formula ##STR20## wherein R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, one of A and B is characterized by the formula SR.sup.* where R.sup.* is branched chain lower alkyl or lower alkenyl, and the other is hydrogen,
- n is 0-6;
- and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Compounds of the formula ##STR21## wherein A and B are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is not hydrogen, and
- R.sup.* is H or lower alkyl.
Compounds of claim 26 wherein B is hydrogen and A is tertiary butyl.
The compounds of the formula ##STR22## wherein A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, or SR.sup.* where R.sup.* is lower alkyl cycloalkyl or lower alkenyl, with the proviso that one of A and B is SR.sup.* and
- R.sup.** is H or lower alkyl.
Dependencies are inferred from the claim text.