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US 6,320,047 B1Granted
Substituted aryl or heteroarylamides having retinoid-like biological activity
AssigneeAllergan Sales, Inc.
InventorsMin Teng, Tien T. Duong, Roshantha A. Chandraratna
Life of this patent
Estimating the term…
Abstract
Compounds of the formula wherein the symbols have the meaning described in the specification, have retinoid-like biological activity.
Claims13
A compound of the formula
- wherein R1 is independently H or alkyl of 1 to 6 carbons;
- m is an integer having the value of 0-5;
- p is an integer having the value of 0-2;
- r is an integer having the value 0-2;
- Z is O or S;
- Y is a naphthyl group, or heteroaryl selected from a group consisting of pyridazinyl, pyrimidinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said naphthyl and heteroaryl groups being optionally substituted with one or two R1 groups;
- W is a substituent selected independently from the group consisting of F, Br, Cl, I, C1-6alkyl, fluoro substituted C1-6 alkyl, NO2, N3, OH, OCH2OCH3, OC1-10alkyl, tetrazol, CN, SO2C1-6-alkyl, SO2C1-6-fluoro substituted alkyl, SO-C1-6 alkyl, CO-C1-6alkyl, COOR8, phenyl, phenyl itself substituted with a W group other than with phenyl or substituted phenyl;
- 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, and
- B is COOH or a pharmaceutically acceptable salt thereof, COOR8, CONRR10 , —CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, —COR7, CR7OR12)2, CR7OR13O, 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 trimethylsilylalkyl 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.
6 more elements
A compound of the formula
- wherein R1 is independently H or alkyl of 1 to 6 carbons;
- m is an integer having the value of 0-5;
- p is an integer having the value of 0-2;
- r is an integer having the value 0-2;
- Z is O or S;
- W is a substituent selected independently from the group consisting of F, Br, Cl, I, C1-6alkyl, fluoro substituted C1-6 alkyl, NO2, N3, OH, OCH2CH3, OC1-10alkyl, tetrazo CN, SO2C1-6-alkyl, SO2C1-6-fluoro substituted alkyl, SO—C1-6 alkyl CO-C1-6alkyl, COOR8, phenyl, phenyl itself substituted with a W group other than with phenyl or substituted phenyl;
- 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, and
- B is COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, —CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, —COR7, CR7(OR12)2, CR7OR13O, 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 trimethylsilylalkyl 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, with the proviso that the —NH—CO— group is attached to 2 or 4 or 5 or 6 position of the pyridine ring.
5 more elements
Dependencies are inferred from the claim text.