Lanthionine-related compounds for the treatment of inflammatory diseases
AssigneeOklahoma Medical Research Foundation
InventorKenneth Hensley
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Abstract
The present invention provides compositions comprising lanthionine ketimine derivatives and thiomorpholine dicarboxylic acid derivatives, as well as processes for the preparation of such compounds. The invention also concerns the use of lanthionine, lanthionine ketimine (LK), LK derivatives, thiomorpholine dicarboxylic acid (TMDCA), and TMDCA derivatives. It concerns the use of these compounds for the treatment and/or prevention diseases, including diseases affecting the central nervous system. The invention provides for compounds and methods having anti-oxidant, anti-neuroinflammatory and neuroprotective activities. It also provides for compounds having the ability to pass through and/or be transported through cellular membranes, such the blood-brain barrier.
Claims38
A compound having the structure:
- wherein R1 is —OH, —NH2, —OCH3, —OCH2CH2CH3, —OCH(CH3)2, —OCH(CH2)2, or heteroatom substituted or unsubstituted versions of C2-C10-alkenyloxy, C2-C10-alkynyloxy, C1-C10-aryloxy, C2-C10-aralkoxy, C1-C10-acyloxy, C1-C10-alkylamino, C2-C10-alkenylamino, C2-C10-alkynylamino, C1-C10-arylamino, C2-C10-aralkylamino, or C1-C10-amido;
- wherein R2 is —OH, —NH2, or heteroatom substituted or unsubstituted versions of C2-C10-alkoxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy, C1-C10-aryloxy, C2-C10-aralkoxy, C1-C10 -acyloxy, C1-C10-alkylamino, C2-C10-alkenylamino, C2-C10-alkynylamino, C1-C10-arylamino, C2-C10-aralkylamino, or C1-C10-amido;
- provided that R1 and R2 are not both —OH;
- is —OCH3 and R1 is —OH, then the compound is predominantly one enantiomer, and
- pharmaceutically acceptable salts and optical isomers thereof.
A compound having the structure:
- wherein:
- R1 is —OH, —NH2, or heteroatom substituted or unsubstituted versions of C1-C10-alkoxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy, C1-C10-aryloxy, C2-C10-aralkoxy, C1-C10-acyloxy, C1-C10-alkylamino, C2-C10-alkenylamino, C2-C10-alkynylamino, C1-C10-arylamino, C2-C10-aralkylamino, or C1-C10-amido;
- R2 is —OH, or heteroatom substituted or unsubstituted versions of C2-C10-alkenyloxy, C1-C10-alkynyloxy, C1-C10-aryloxy, C2-C10-aralkoxy, C1-C10-acyloxy, C1-C10-alkylamino, C2-C10-alkenylamino, C2-C10-alkynylamino, C1-C10-arylamino, C2-C10-aralkylamino, or C1-C10-amido;
- provided that R1 and R2 are not both —OH;
- or pharmaceutically acceptable salts, and optical isomers thereof.
Dependencies are inferred from the claim text.