Substituted aryl or heteroarylamides having retinoid-like biological activity
First Claim
Patent Images
1. A compound of the formula 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 0-2;
r is an integer having the value 0-2;
L is —
(C═
Z)—
NH—
or —
NH—
(C═
Z)—
where Z is O or S;
Y is pyrazinyl, optionally substituted with one or two R1 groups;
W is a substituent selected 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-alkyl, SO2C1-6-fluoro substituted alkyl, SO-C1-6alkyl, 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 if B represents COOH then W is not Cl.
1 Assignment
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Accused Products
Abstract
Compounds of the formula
wherein X, L, Y, A, B, W, R1, m, p and r are defined above.
104 Citations
11 Claims
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1. A compound of the formula
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 0-2;
r is an integer having the value 0-2;
L is —
(C═
Z)—
NH—
or —
NH—
(C═
Z)—
where Z is O or S;
Y is pyrazinyl, optionally substituted with one or two R1 groups;
W is a substituent selected 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-alkyl, SO2C1-6-fluoro substituted alkyl, SO-C1-6alkyl, 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 if B represents COOH then W is not Cl.- View Dependent Claims (2, 3, 4, 5, 6)
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7. A compound of the formula
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 0-2;
r is an integer having the value 0-2;
L is —
(C═
Z)—
NH—
where Z is O or S;
Y is furyl, optionally substituted with one or two R1 groups;
W is a substituent selected 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-alkyl, SO2C1-6-fluoro substituted alkyl, SO—
C1-6alkyl, 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 if B represents COOH then W is not Cl.
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8. A compound of the formula
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 0-2;
r is an integer having the value 1-2;
L is —
(C═
Z)—
NH—
or —
NH—
(C═
Z)—
where Z is O or S;
Y is furyl, optionally substituted with one or two R1 groups;
W is a substituent selected 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-alkyl, SO2C1-6-fluoro substituted alkyl, SO—
C1-6alkyl, 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.- View Dependent Claims (9, 10, 11)
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Specification