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US 7,067,539 B2Granted
Cannabinoid receptor ligands
AssigneeSchering Corporation
InventorsJoseph A. Kozlowski, Neng-Yang Shih, Brian J. Lavey, Razia K. Rizvi, Bandarpalle B. Shankar, James M. Spitler, Ling Tong, Ronald L. Wolin, Michael K. Wong
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Abstract
The invention relates to compounds of the formula a prodrug thereof, or a pharmaceutically acceptable salt, solvate or stereoisomer of the compound or of said prodrug; which exhibit anti-inflammatory and immunodulatory activity. Also disclosed are pharmaceutical compositions containing said compounds and methods of using the compounds for the treatment of various diseases and conditions.
Claims31
A compound of the formula
- or a pharmaceutically acceptable salt or solvate thereof;
- wherein:
- R1 is selected from the group consisting of H, alkyl, haloC1–C6alkyl, cycloalkyl, cycloalkylNH—, arylalkyl, heterocycloalkyl, heteroaryl, —N(R2)2, —N(R2)aryl, unsubstituted aryl and aryl substituted with one to three X, wherein each R2 can be the same or different and is independently selected when there are more than one R2 present;
- R2 is selected from the group consisting of H and C1–C6 alkyl;
- R3 is 1–3 substituents selected from the group consisting of H, C1–C6 alkyl, Cl, F, CF3, OCF2H, OCF3, OH and C1–C6 alkoxy, wherein R3 can be the same or different and is independently selected when there are more than one R3 present;
- R4 is pyridine-N-oxide or pyridyl optionally substituted with one to three X, wherein X can be the same or different and is independently selected when there are more than one X present;
- R5 is H or C1–C6 alkyl;
- R6 is H or C1–C6 alkyl;
- or
- R5 and R6 taken together with the carbon atom to which they are attached form a carbonyl group;
- L1 is —SO2—, —SO—, or —S—;
- L2 is —SO2—, —SO—, or —S—;
- X is selected from the group consisting of H, halogen, CF3, CN, OCF2H, OCF2CF3, OCF3, OR2, C1–C6 alkyl, cycloalkyl, cycloalkoxy, C1–C6 alkoxy, alkoxyC1–C6 alkoxy, O-cycloalkyl, cycloalkylamino, cycloalkylalkoxy, heteroalkyl, —OSO2R2,
- —COOR2, —CON(R2)2, N(R2)2, and NR2aryl, wherein X can be the same or different, and is independently selected when there are more than one X present;
- Y is a covalent bond, —CH2—, —SO2—, or —C(O)—;
- Z is a covalent bond, —CH2—, —SO2— or —C(O)—;
- or
- Y, R1, Z and R2 can be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl;
- with the following provisos:
- L2 and R4, when taken together, cannot have two heteroatoms covalently bonded together;
- when R2 is H, Z cannot be —S(O)—, —SO2—, or —C(O)—;
- and
- when Y is a covalent bond, R1 cannot form a N—N bond with the nitrogen atom.
20 more elements
Dependencies are inferred from the claim text.