Tetralin esters of phenols or benzoic acids having retinoid like activity
AssigneeAllergan, Inc.
InventorsRoshantha A. S. Chandraratna, Robert J. Weinkam
Life of this patent
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Abstract
Retinoid-like activity is exhibited by compounds of the formula ##STR1## where the R groups are independently hydrogen, or lower alkyl; A is --C(O)O--, --OC(O)--, --C(O)S--, or --SC(O)--; n is 0-5; and Z is H, --COB where B is --OH or a pharmaceutically acceptable salt, or B is --OR.sub.1 where R.sub.1 is an ester-forming group, or B is --N(R).sub.2 where R is hydrogen or lower alkyl, or Z is --OE where E is hydrogen or an ether-forming group or --COR.sub.2 where R.sub.2 is hydrogen, lower alkyl, phenyl or lower alkyl phenyl, or Z is --CHO or an acetal derivative thereof, or Z is --COR.sub.3 where R.sub.3 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4 and the sum of n and m does not exceed 4.
Claims17
A compound of the formula ##STR9## where the R groups are independently hydrogen, or lower alkyl;
- n is 0-5;
- and Z is --COB where B is --OH or a pharamaceutically acceptable salt, or B is --OR.sub.1 where R.sub.1 is an ester-forming group, or B is --N(R).sub.2 where R is independently hydrogen or lower alkyl, or Z is OE where E is hydrogen or COR.sub.2 where R.sub.2 is hydrogen, lower alkyl, phenyl or lower alkyl phenyl, or Z is --CHO or an acetal derivative thereof, or Z is COR.sub.3 where R.sub.3 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4 and the sum of n and m does not exceed 4.
Ethyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate.
4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)-benzoic acid or a pharmaceutically acceptable salt thereof.
4-methoxymethylphenyl-5,5,8,8-tetramethyl-5, 6,7,8-tetrahydro-2-naphthoate or 4-dimethoxymethylphenyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoat e.
4-(5,5,8,8-tetramethyl-5,6,7,8tetrahydro-2-naphthoyloxy) benzamide.
4-(8,8-dimethyl-5,6,7,8-tetrahydro 2-naphthoyloxy)-benzoic acid or a pharmaceutically acceptable salt thereof, ethyl 4-(8,8-dimethyl -5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate, or benzyl(8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate.
4-(5,5-dimethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)-benzoic acid or a pharmaceutically acceptable salt thereof, ethyl 4-(5,5-dimethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate, or benzyl 4-(8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate.
4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)-benzoic acid or a pharmaceutically acceptable salt thereof.
Ethyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate or benzyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate.
4-methoxymethylphenyl-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphth oate or 4-formylphenyl 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthoate.
Dependencies are inferred from the claim text.