Cannabinoid receptor CB2 ligand 4-(aminomethyl)-N, N-dialkylanilines
AssigneeUniversity of Pittsburgh—Of the Commonwealth System of Higher Education
InventorsXiang-Qun Xie, Abdulrahman Almehizia, Peng Yang
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Abstract
Disclosed herein are novel cannabionid receptor-2 (CB2) agonists and inverse agonists represented by Formula (I), and method of modulating the activity of CB2 by contacting the CB-2 receptor with a compound of Formula (I). Also, disclosed are methods for treating multiple myeloma or osteoporosis in a mammal in need thereof by modulating the activity of a cannabinoid receptor-2 (CB2).
Claims21
A method for treating multiple myeloma in a mammal in need thereof by modulating the activity of a cannabinoid receptor-2 (CB2), comprising administering to the mammal a therapeutically effective amount of a compound represented by Formula (I):
- wherein:
- R is A-B-Y;
- A is —SO2— or —C(O)—;
- B is a bond or —CHCH—;
- X is selected from the group consisting of substituted phenyl, substituted or unsubstituted pyridine, and substituted or unsubstituted C3-5 alkyl, wherein the substituted phenyl, pyridine and alkyl is substituted with two or three moieties selected from C1-4 alkyl, C1-4 alkoxy, —C(O)H, C1-4 perfluroalkyl, and C1-4 perfluroalkoxy, or the substituted phenyl or pyridine is substituted with —O—(CH2)1-2—O— where the O molecules are covalently bound to adjacent carbon atoms on the substituted phenyl or pyridine;
- Y is a ringed moiety selected from phenyl, naphthyl, and thiophenyl, wherein one or two of the ring carbons is optionally replaced with N, and wherein the ringed moiety is optionally substituted with one to three C1-4 alkyl, C1-4 alkoxy, —C(O)H, C1-4 perfluroalkyl, C1-4 perfluroalkoxy, or substituted or unsubstituted phenyl;
- and
- R′ is, in each instance a C1-6 alkyl,
- or a pharmaceutically acceptable salt thereof.
A method for treating osteoporosis in a mammal in need thereof by modulating the activity of a cannabinoid receptor-2 (CB2), comprising administering to the mammal a therapeutically effective amount of a compound represented by Formula (I):
- wherein:
- R is A-B-Y;
- A is —SO2— or —C(O)—;
- B is a bond or —CHCH—;
- X is selected from the group consisting of substituted phenyl, substituted or unsubstituted pyridine, and substituted or unsubstituted C3-5 alkyl, wherein the substituted phenyl, pyridine and alkyl is substituted with two or three moieties selected from C1-4 alkyl, C1-4 alkoxy, —C(O)H, C1-4 perfluroalkyl, and C1-4 perfluroalkoxy, or the substituted phenyl or pyridine is substituted with —O—(CH2)1-2—O— where the 0 molecules are covalently bound to adjacent carbon atoms on the substituted phenyl or pyridine;
- Y is a ringed moiety selected from phenyl, naphthyl, and thiophenyl, wherein one or two of the ring carbons is optionally replaced with N, and wherein the ringed moiety is optionally substituted with one to three C1-4 alkyl, C1-4 alkoxy, —C(O)H, C1-4 perfluroalkyl, C1-4 perfluroalkoxy, or substituted or unsubstituted phenyl;
- and
- R′ is, in each instance a C1-6 alkyl,
- or a pharmaceutically acceptable salt thereof.
A method for modulating the activity of a cannabinoid receptor-2 (CB2) in a mammal in need thereof, comprising contacting the CB-2 receptor with a compound represented by Formula (I):
- wherein:
- R is A-B-Y;
- A is —SO2— or —C(O)—;
- B is a bond or —CHCH—;
- X is selected from the group consisting of substituted phenyl, substituted or unsubstituted pyridine, and substituted or unsubstituted C3-5 alkyl, wherein the substituted phenyl, pyridine and alkyl is substituted with two or three moieties selected from C1-4 alkyl, C1-4 alkoxy, —C(O)H, C1-4 perfluroalkyl, and C1-4 perfluroalkoxy, or the substituted phenyl or pyridine is substituted with —O—(CH2)1-2—O— where the O molecules are covalently bound to adjacent carbon atoms on the substituted phenyl or pyridine;
- Y is a ringed moiety selected from phenyl, naphthyl, and thiophenyl, wherein one or two of the ring carbons is optionally replaced with N, and wherein the ringed moiety is optionally substituted with one to three C1-4 alkyl, C1-4 alkoxy, —C(O)H, C1-4 perfluroalkyl, C1-4 perfluroalkoxy, or substituted or unsubstituted phenyl;
- and
- R′ is, in each instance a C1-6 alkyl,
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.