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US 5,475,113 AGranted
Tetrahydronaphthyl and thiazole, oxazole or imidazole substituted ethene derivatives having retinoid-like activity, reduced skin toxicity and reduced teratogenecity
AssigneeAllergan, Inc.
InventorRoshantha A. Chandraratna
Life of this patent
Estimating the term…
Abstract
Compounds of the formula ##STR1## as herein defined, have retinoid-like activity and are substantially non-teratogenic and non-irritating to the skin.
Claims32
A compound of the formula ##STR11## where R.sub.1 is lower alkyl, Cl, Br, or I;
- R.sub.2 is H, lower alkyl, Cl, Br, or I;
- R.sub.3 is lower alkyl, Cl, Br, I, OR.sub.11, SR.sub.11, OCOR.sub.11, SCOR.sub.11, NH.sub.2, NHR.sub.11, N(R.sub.11).sub.2, NHCOR.sub.11, or NR.sub.11 --COR.sub.11 ;
- R.sub.5 and R.sub.6 independently are H, lower alkyl, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1 to 6 carbons;
- A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds;
- B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.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.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 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 alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons;
- R.sub.2O is independently H or lower alkyl, and
- Y is oxazole, thiazole, imidazole, isothiazole or isoimidazole which may be optionally substituted on a carbon or on a nitrogen with an R.sub.21 group which is lower alkyl, or SO.sub.2 NR.sub.22 R.sub.23 where R.sub.22 is lower alkyl and R.sub.23 is hydrogen or lower alkyl.
4 more elements
A compound of the formula ##STR12## where R.sub.1 is lower alkyl;
- R.sub.2 is H or lower alkyl;
- R.sub.3 is lower alkyl, Cl, Br, or I, and
- B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, or CONR.sub.9 R.sub.10, where 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.
A compound of the formula ##STR13## where R.sub.1 is lower alkyl;
- R.sub.2 is H or lower alkyl;
- R.sub.3 is lower alkyl, Cl, Br, or I, and
- B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, or CONR.sub.9 R.sub.10, where 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, and
- R.sub.21 is H, or lower alkyl, or SO.sub.2 NR.sub.22 R.sub.23 where R.sub.22 is lower alkyl and R.sub.23 is hydrogen or lower alkyl.
1 more element
Dependencies are inferred from the claim text.