Acetylenes disubstituted with a heteroaromatic group and a 2-substituted 1,2,3,4-tetrahydroquinolinyl group 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 X is S, O or NR'; where R' is hydrogen or lower alkyl; R.sub.1, R.sub.2 and R.sub.3 are hydrogen or lower alkyl; R.sub.4 and R.sub.5 are hydrogen or lower alkyl with the proviso that R.sub.4 and R.sub.5 cannot both be hydrogen, A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl; n is 0-5, and B 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.sub.1 or aketal derivative where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 were m is 0-4, or a pharmaceutically acceptable salt thereof.
Claims18
Compounds of the formula ##STR9## where X is NR', where R' is hydrogen or lower alkyl;
- R.sub.1, R.sub.2 and R.sub.3 are hydrogen or lower alkyl;
- R.sub.4 and R.sub.5 are hydrogen or lower alkyl with the proviso that R.sub.4 and R.sub.5 both are not hydrogen;
- n is an integer from 0 to 5;
- A is selected from a group consisting of pyridinyl, thiazolyl and oxazolyl, and
- B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, COONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR", CR"(OR.sub.12).sub.2, or CR"OR.sub.13 O, where R" is an alkyl group having 1-5 carbons, cycloalkyl having 3-5 carbons or alkenyl group having 2 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, R.sub.13 is divalent alkyl radical of 2-5 carbons.
Dependencies are inferred from the claim text.