Substituted heteroarylamides having retinoid-like biological activity
First Claim
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1. A compound of the formula ##STR10## wherein X is N;
- 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 1 or 2;
r is an integer having the value 0-2;
L is --(C═
Z)--NH--where Z is O or S;
Y is phenol 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 -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 with the proviso that at least one W group that substitutes the pyridine ring is alkyl;
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
19 Claims
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1. A compound of the formula ##STR10## wherein X is N;
- 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 1 or 2; r is an integer having the value 0-2; L is --(C═
Z)--NH--where Z is O or S;Y is phenol 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 -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 with the proviso that at least one W group that substitutes the pyridine ring is alkyl; 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, 3, 4, 5)
- R1 is independently H or alkyl of 1 to 6 carbons;
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6. A compound of the formula ##STR11## wherein X is N;
- 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 1 or -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, C1-6 alkyl, fluoro substituted C1-6 alkyl, NO2, N3, OH, OCH2 OCH3, OC1-10 alkyl, tetrazol, CN, SO2 C1-6 -alkyl, 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 with the proviso that at least one W group that substitutes the pyridine ring is branch-chained alkyl; 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 OCHR11, 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 (7, 8, 9, 10, 17)
- R1 is independently H or alkyl of 1 to 6 carbons;
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11. A compound of the formula ##STR12## wherein X is N;
- W1 is H or OH;
W2 is H, F or NO2 ; W, is H, F or NO2 ; R8 is H, CH3 or C2 H5 [, with the proviso that when X is CH then W1, W2 and W3 all are not H]. - View Dependent Claims (12, 13, 14, 15, 16, 18, 19)
- W1 is H or OH;
Specification