Ring-labeled retinoids and intermediates, and methods for their synthesis and use
AssigneeLigand Pharmaceuticals Incorporated
InventorsYoussef L. Bennani, Marcus F. Boehm
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Abstract
Methods for the synthesis of dideuterium and/or ditritium ring-labeled retinoids and intermediates, and their use in the discovery of Retinoid X Receptor ligands are provided. In addition, dideuterium and/or ditritium ring-labeled retinoids and novel intermediates, as well as methods for their use in ligand binding and mass spectral studies are also provided.
Claims9
A ring-labeled retinoid of the general formula:
- ##STR3## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each can independently represent hydrogen or a lower straight chain or branched alkyl, aryl, heteroaryl or aralkyl having 1-12 carbon atoms;
- R.sup.7 represents hydrogen or a pharmaceutically acceptable salt, n=2 or 3;
- and 9-10, 11-12 and 13-14 olefin bonds are in either the trans or cis configuration.
A ring-labeled retinoid selected from the group consisting of ethyl (2E,4E,6Z,8E)-3,4- .sup.3 H.sub.2 !-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate , ethyl (2E,4E,6Z,8E)-4,5- .sup.3 H.sub.2 !-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate , (2E,4E,6Z,8E)-4,5- .sup.3 H.sub.2 !-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid, (2E,4E,6Z,8E)-4,5- .sup.3 H.sub.2 !-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid, ethyl (2E,4E,6Z,8E)-3,4- (2E,4E,6Z,8E)-4,5- .sup.3 H.sub.2 !-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate , ethyl (2E,4E,6Z,8E)-3,4- .sup.2 H.sub.2 !-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate , (2E,4E,6Z,8E)-3,4- .sup.3 H.sub.2 !-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid, and (2E,4E,6Z,8E)-3,4- .sup.2 H.sub.2 !-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid.
Dependencies are inferred from the claim text.