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US 6,388,105 B1Granted
Benzofuran, indole or benzothiophene 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors
AssigneeAllergan Sales, Inc.
InventorsVidyasagar Vuligonda, Roshantha A. Chandraratna
Life of this patent
Estimating the term…
Abstract
Compounds of the formula Where the variables are defined as in the specification, are selective agonists of RXR retinoid receptors.
Claims30
A compound of the formula
- X is O, NR′ or S where R′ is alkyl of 1 to 6 carbons;
- Y is a bivalent cyclopropyl radical optionally substituted with one or two R4 groups, or Y is a bivalent aryl or 5 or 6 membered heteroaryl radical having 1 to 3 heteroatoms selected from N, S and O, said aryl or heteroaryl groups optionally substituted with 1 to 4 R4 groups;
- R1 is independently H, alkyl of 1 to 6 carbons, or fluoroalkyl of 1 to 6 carbons;
- R2 is alkyl of 1 to 8 carbons, or fluoroalkyl of 1 to 8 carbons;
- R′2 is alkyl of 1 to 8 carbons, or fluoroalkyl of 1 to 8 carbons;
- R3 is hydrogen, alkyl of 1 to 6 carbons, fluoro substituted alkyl of 1 to 6 carbons, halogen, alkoxy of 1 to 8 carbons, or alkylthio of 1 to 6 carbons;
- NO2, NH2, NHCO(C1-C6 alkyl, NHCO(C1-C6)alkenyl, NR1H or N(R1)2, benzyloxy or C1-C6alkyl-substituted benzyloxy;
- R4 is H or alkyl of 1 to 6 carbons, or fluoro substituted alkyl of 1 to 6 carbons;
- m is an integer having the values of 0 to 3, and
- B is COOH or a pharmaceutically acceptable salt thereof, COOR8, COOCH2COR7, CONR9R10, —CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CH(OR13O), —COR7, CR7(OR12)2, CR7(OR13O), 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, hydroxyphenyl 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
A compound of the formula
- where R1 is independently H, alkyl of 1 to 6 carbons, or fluoroalkyl of 1 to 6 carbons;
- R2 is alkyl of 1 to 8 carbons, or fluoroalkyl of 1 to 8 carbons;
- R′2 is alkyl of 1 to 8 carbons, or fluoroalkyl of 1 to 8 carbons;
- R3 is hydrogen, alkyl of 1 to 6 carbons, fluoro substituted alkyl of 1 to 6 carbons, halogen, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- NO2, NH2, NHCO(C1-C6 alkyl, NHCO(C1-C6)alkenyl, NR1H or N(R1)2;
- R4 is H or alkyl of 1 to 6 carbons, or fluoro substituted alkyl of 1 to 6 carbons;
- m is an integer having the values of 0 to 3, and
- B is COOH or a pharmaceutically acceptable salt thereof, COOR8, COOCH2COR7, CONR9R10, —CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CH(OR13O), —COR7, CR7(OR12)2, CR7(OR13O), 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, hydroxyphenyl 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.
5 more elements
A compound of the formula
- where R2 is alkyl of 1 to 6 carbons;
- R′2 is alkyl of 1 to 6 carbons, and
- R′8 is COOH or a pharmaceutically acceptable salt thereof, or COOR8 where R8 is alkyl of 1 to 6 carbons.
Dependencies are inferred from the claim text.