Cannabinoid Receptor Modulating Compounds
AssigneeThe United States of America, as represented by the Secretary, Department of Health and Human
InventorsMalliga R. Iyer, George Kunos, Resat Cinar
Life of this patent
Estimating the term…
Abstract
In accordance with the purpose(s) of the present disclosure, as embodied and broadly described herein, the disclosure, in one aspect, relates to sulfur- and selenium-containing compounds that act as agonists and/or antagonists of cannabinoid receptors, methods of making same, pharmaceutical compositions comprising the same, and methods of treating metabolic disorders, psychiatric disorders, neurological disorders, pain disorders, gastrointestinal disorders, cancers, inflammation-related disorders, substance abuse associated pathologies, and other conditions using the same.
Claims24
A compound comprising a structure of Formula I
- wherein X is naphthyl, heteroaryl, linear or branched C1-C10 alkyl, or
- wherein each of R1a—R1e independently is selected from hydrogen, halogen, hydroxy, C1-C6 alkyl, —CF3, —OCF3, —O—(C1-C6 alkyl), —NO2, or —CN;
- wherein Y1 and Y2 independently are hydrogen, naphthyl, heteroaryl, linear or branched C1-C10 alkyl, or
- provided Y1 and Y2 are not both hydrogen;
- wherein each of R2a—R2e independently is selected from hydrogen, halogen, hydroxy, C1-C6 alkyl, fluoroalkyl, fluoroalkoxy, —O—(C1-C6 alkyl), —NO2, or —CN;
- wherein Z1 and Z2 independently are hydrogen, —CO(═O)—(C1-C6 alkyl), or —C(═O)NH—(C1-C6 alkyl);
- wherein Q is —S—R3, —S(═O)—R3, —S(═O)2—R3, —(CH2)x—R3, —Se—R3, —Se(═O)—R3, or —Se(═O)2—R3, or OR3;
- wherein R3 is selected from hydrogen, substituted or unsubstituted branched or linear C1-C6 alkyl, C1-C6 alkene, C1-C6 alkyne, C1-C6 allene, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, —(C(R14a)(R14b))x—C(═O)—N(R13a)(R13b), —(C(R14a)(R14b))y—C(═O)—NHOH, or —(C(R14a)(R14b))y—CH(CH3)—C(═O)(OR10);
- —(CH2)yCN, —(CH2)yNO2, —(CH2)yNHNH2, —(C(R14a)(R14b))ySO3R, —(C(R14a)(R14b))yN3, —(C(R14a)(R14b))y—C2H2N3, —(C(R14a)(R14b))ySON(R13a)(R13b), —(C(R14a)(R14b))ySO2N(R13a)(R13b), —(C(R14a)(R14b))yPON(R13a)(R13b), —(C(R14a)(R14b))yPO(OR15)NR16, —(C(R14a)(R14b))yB(OR15)3, —(C(R14a)(R14b))y(C═NR16)N(R13a)(R13b), C1-C6 alkoxy, OC(R17)3, OSi(R17)3, or —OCHF2;
- wherein x is from 1 to 6;
- wherein y is from 0 to 6;
- wherein R10 is C1-C6 alkyl;
- wherein each of R13a, R13b, R14a, R14b, R15, R16, and R17, when present, is independently selected from hydrogen, halogen, hydroxy, C1-C6 alkyl, fluoroalkyl, fluoroalkoxy, —O—(C1-C6 alkyl), —NO2, or —CN;
- provided that when Q is —S—R3, R3 is not linear or branched alkyl;
- wherein A is —SO2—R4, —SeO2—R4—S(═O)—R4, —S(═O)(—R4)(—R5), —S(═O)(═NH)—R4, —C(═O)—R4, —Se—R4, —Se(═O)—R4, —Se(═O)(—R4)(—R5), or —N(R19a)(R19b);
- wherein R4 is
- wherein each of R19a and R19b is independently selected from hydrogen, halogen, hydroxy, substituted or unsubstituted C1-C6 alkyl, fluoroalkyl, fluoroalkoxy, —O—(C1-C6 alkyl), —NO2, or —CN, and wherein R19b is optionally absent;
- wherein each of R20a and R20b is independently selected from linear or branched C1-C6 alkyl or adamantyl;
- wherein each of R12a and R12b independently is hydrogen, CF3, phenyl, fluoro, or any combination thereof;
- wherein U is NR13, S, SO2, or O;
- wherein R18 is selected from hydrogen, halogen, hydroxy, C1-C6 alkyl, fluoroalkyl, fluoroalkoxy, —O—(C1-C6 alkyl), —NO2, or —CN;
- wherein each of Rea-R6e independently is selected from hydrogen, halogen, hydroxy, C1-C6 alkyl, fluoroalkyl, fluoroalkoxy, —O—(C1-C6 alkyl), —NO2, —CN, —(CH2)z-R7, naphthyl, or heteroaryl;
- wherein R7 is halogen, —CN, fluoroalkyl, fluoroalkoxy, or alkoxy;
- wherein z is from 1 to 3;
- wherein R5 is (═O), —NH—R8, or
- wherein R8 is hydrogen or C1-C6 alkyl;
- and
- wherein each of R9a and R9b independently is hydrogen or halogen.
(canceled)
(canceled)
(canceled)
-45. (canceled)
Dependencies are inferred from the claim text.