Substituted aryl or heteroarylamides having retinoid-like biological activity
First Claim
Patent Images
1. A compound of the formula ##STR10## wherein X is CH;
- 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 a phenyl or naphthyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said phenyl, 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, C1-6 alkyl, fluoro substituted C1-6 alkyl, NO2, N3, OCH2 OCH3, tetrazol, CN, SO2 C1-6 -fluoro substituted alkyl, SO--C1-6 alkyl, COOR8, phenyl, phenyl itself substituted with a W group other than with phenyl or substituted phenyl with the proviso that when r is 0 then p is not 0 and at least one W group is not 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 allylphenyl, R12 is lower alkyl, and R13 is divalent alkyl radical of 2-5 carbons.
1 Assignment
0 Petitions
Accused Products
Abstract
Compounds of the formula ##STR1## wherein the symbols have the meaning described in the specification, have retinoid-like biological activity.
106 Citations
21 Claims
-
1. A compound of the formula ##STR10## wherein X is CH;
- 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 a phenyl or naphthyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said phenyl, 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, C1-6 alkyl, fluoro substituted C1-6 alkyl, NO2, N3, OCH2 OCH3, tetrazol, CN, SO2 C1-6 -fluoro substituted alkyl, SO--C1-6 alkyl, COOR8, phenyl, phenyl itself substituted with a W group other than with phenyl or substituted phenyl with the proviso that when r is 0 then p is not 0 and at least one W group is not 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 allylphenyl, R12 is lower alkyl, and R13 is divalent alkyl radical of 2-5 carbons. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8)
- R1 is independently H or alkyl of 1 to 6 carbons;
-
9. A compound of the formula ##STR11## wherein X is CH;
- 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, C1-6 alkyl, fluoro substituted C1-6 alkyl, NO2, N3, OCH2 OCH3, tetrazol, CN, SO2 C1-6 -fluoro substituted alkyl, SO--C1-6 alkyl, COOR8, phenyl, phenyl itself substituted with a W group other than with phenyl or substituted phenyl with the proviso that when r is 0 then p is not 0 and at least one W group is not 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 (10, 11, 12, 13)
- R1 is independently H or alkyl of 1 to 6 carbons;
-
14. A compound of the formula ##STR12## wherein X is CH;
- W1 is H or OH;
W2 is H, F or NO2 ; W3 is H, F or NO2 ; R8 is H, CH3 or C2 H5, with the proviso that at least one of W1, W2 and W3 is F. - View Dependent Claims (20)
- W1 is H or OH;
-
15. A compound of the formula ##STR13## wherein X is CH;
- W1 is H or OH;
W2 is F and W3 is H, and R8 is H, CH3 or C2 H5 or a pharmaceutically acceptable salt thereof. - View Dependent Claims (17, 21)
- W1 is H or OH;
-
16. A compound of the formula ##STR14## wherein X is CH;
- W1 is H or OH;
W2 is NO2 ; W3 is H, F, or NO2, and R8 is H, CH3 or C2 H5 or a pharmaceutically acceptable salt thereof.
- W1 is H or OH;
-
18. A compound of the formula ##STR15## wherein X is CH;
- W1 is H or OH;
W2 is F; W3 is F; and R8 is H, CH3 or C2 H5 or a pharmaceutically acceptable salt thereof. - View Dependent Claims (19)
- W1 is H or OH;
Specification
-
- Resources
Litigation Campaign Assessment
Thank you for your request. You will receive a custom alert email when the Litigation Campaign Assessment is available.
×
-
Current AssigneeAllergan, Inc. (Canada) (Abbvie Incorporated)
-
Original AssigneeAllergan Sales LLC (Abbvie Incorporated)
-
InventorsTeng, Min, Chandraratna, Roshantha A., Duong, Tien T.
-
Primary Examiner(s)NORTHINGTON DAVIS, ZINNA
-
Application NumberUS08/820,792Time in Patent Office832 DaysField of Search546/309, 546/323, 564/74, 564/161, 544/229, 544/322, 544/335, 544/406, 544/407, 549/69, 549/79, 549/480, 549/487, 548/192, 548/200, 548/233, 548/236, 548/326.5, 548/338.1, 548/372.5, 548/374.5US Class Current546/309CPC 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
