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US 6,538,149 B1Granted
Aryl or heteroaryl substituted 3,4-dihydroanthracene and aryl or heteroaryl substituted benzo [1,2-g]chrom-3-ene, benzo[1,2-g]-thiochrom-3-ene and benzo [1,2-g]-1,2-dihydroquinoline derivatives having retinoid antagonist or retinoid inverse agonist type biological activity
AssigneeAllergan, Inc.
InventorsVidyasagar Vuligonda, Alan T. Johnson, Roshantha A. Chandraratna
Life of this patent
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Abstract
Compounds of the formula where the symbols have the meaning defined in the specification, have retinoid, retinoid antagonist and/or retinoid inverse-agonist-like biological activity.
Claims4
A compound of the formula
- where
- R1 is independently H or alkyl of 1 to 6 carbons;
- R2 is optional and is defined as lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- n is an integer between 0 and 2;
- o is an integer between 0 and 3;
- R3 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br or I;
- R4 is phenyl, (R5)p-phenyl, naphthyl, or (R5)p-naphthyl, [heteroaryl or (R5)p-heteroaryl where the heteroaryl group is pyridyl, thienyl, furyl or thiazolyl];
- p is an integer having the values of 0-5;
- R5 is optional and is defined as independently F, Cl, Br, I, NO2, N(R8)2, N(R8)COR8, NR8CON(R8)2, OH, OCOR8, OR8, CN, COOH, COOR8, an alkyl group having 1 to 10 carbons, or fluoro substituted alkyl group having 1 to 10 carbons;
- A is (CH2)q where q is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds, B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, —CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, —COR7, CR7(OR12)2, CR7OR13O, or Si(C1-6 alkyl)3, where R7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R8 is an alkyl group of 1 to 10 carbons or (trimethylsilyl)alkyl where the alkyl group has 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R8 is phenyl or lower alkylphenyl, R9, and R10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R11 is lower alkyl, phenyl or lower alkylphenyl, R12 is lower alkyl, and R13 is divalent alkyl radical of 2-5 carbons.
7 more elements
Dependencies are inferred from the claim text.