Substituted aryl or heteroarylamides having retinoid-like biological activity
First Claim
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1. A compound of the formula ##STR10## 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;
the pyridyl group bearing the A-B group is optionally substituted with one or two R1 groups;
W is a substituent selected independently from the group consisting of F, Br, Cl, I, C1-6 alkyl, fluoro substituted C1-6 alkyl, NO2, N3, OH, OCH2 OCH3, OC1-10 alkyl, tetrazol, CN, SO2 C1-6 -alkyl, SO2 C1-6 -fluoro substituted alkyl, SO--C1-6 alkyl, CO--C1-6 alkyl, 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, andB is COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9 R10, --CH2 OH, CH2 OR11, CH2 OCOR11, CHO, CH(OR12)2, CHOR13 O, --COR7, CR7 (OR12)2, CR7 OR13 O, 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.
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Abstract
Compounds of the formula ##STR1## wherein the symbols have the meaning described in the specification, have retinoid-like biological activity.
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Citations
4 Claims
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1. A compound of the formula ##STR10## wherein R1 is independently H or alkyl of 1 to 6 carbons;
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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; the pyridyl group bearing the A-B group is optionally substituted with one or two R1 groups; W is a substituent selected independently from the group consisting of F, Br, Cl, I, C1-6 alkyl, fluoro substituted C1-6 alkyl, NO2, N3, OH, OCH2 OCH3, OC1-10 alkyl, tetrazol, CN, SO2 C1-6 -alkyl, SO2 C1-6 -fluoro substituted alkyl, SO--C1-6 alkyl, CO--C1-6 alkyl, 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, CONR9 R10, --CH2 OH, CH2 OR11, CH2 OCOR11, CHO, CH(OR12)2, CHOR13 O, --COR7, CR7 (OR12)2, CR7 OR13 O, 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. - View Dependent Claims (2)
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3. A compound of the formula ##STR11## 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; the thienyl group is optionally substituted with one or two R1 groups; W is a substituent selected independently from the group consisting of F, Br, Cl, I, C1-6 alkyl, fluoro substituted C1-6 alkyl, NO2, N3, OH, OCH2 OCH3, OC1-10 alkyl, tetrazol, CN, SO2 C1-6 -alkyl, SO2 C1-6 -fluoro substituted alkyl, SO--C1-6 alkyl, CO--C1-6 alkyl, 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, CONR9 R10, --CH2 OH, CH2 OR11, CH2 OCOR11, CHO, CH(OR12)2, CHOR13 O, --COR7, CR7 (OR12)2, CR7 OR13 O, 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 I 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. - View Dependent Claims (4)
- m is an integer having the value of 0-5;
Specification
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Current AssigneeAllergan Incorporated (Abbvie Incorporated)
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Original AssigneeAllergan Sales LLC (Abbvie Incorporated)
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InventorsTeng, Min, Chandraratna, Roshantha A., Duong, Tien T.
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Primary Examiner(s)NORTHINGTON DAVIS, ZINNA
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Application NumberUS09/215,509Time in Patent Office488 DaysField of Search546/268.1, 546/14, 546/262, 546/280.4US Class Current546/262CPC Class CodesA61P 35/00 Antineoplastic agentsA61P 43/00 Drugs for specific purposes...C07C 233/81 having the nitrogen atom of...C07D 213/82 in position 3
